We have a mess on our hands

How many homeowners would you say are apathetic vs. apoplectic? If the second group outnumbers the first (I assume you're in that number), that may be enough to make some changes. You already know that won't be easy because everyone else has let things go on for so long, they don't want to deal with the discomfort of making necessary changes. It's human nature - most people know deep down how f***ed up the place is and hope to be out before the caca hits the fan. So fasten your seat belts - this will be a bumpy ride.

Start with reviewing your documents (again) - if you don't see anything about the board, it may be you're looking in the wrong place. The CCRs dictate how the common areas are to be used, whereas the Bylaws dictate how the association is run - that's where you'll see information about the board. If there isn't anything in the paperwork you got at closing, you may want to check with your county recorder's office to see what's on file.

You will need to push for a come to Jesus meeting with the homeowners (all of them) and this is where you and everyone else can express your concerns. From what you've said here, that would be: outdated documents, no board elections, no board meeting minutes (those reflect the official actions of the association and should NEVER be thrown out - the association risks getting into major legal trouble otherwise), assessments that haven't kept up with inflation (which is why your reserves are dangerously low), and a lack of a reserve study (which would give you guidance on how to fund the reserves).

You won't fix everything overnight, but this meeting would be a good time to at least make a plan. There are 16 homeowners, so that's enough for several small groups to be established to take a deep dive on certain issues and make recommendations. One group could address updating the documents, another the trees and roads, a third reviewing finances, etc. There's a lot to do and you can't expect the board (such as it is) to do everything.

Yes, assessments will have to go up - you can't expect 1998 dollars to buy the same amount in 2020 (everyone forgets about inflation). Finally, warn everyone of what could happen if these issues AREN'T addressed - significantly higher costs for everyone and possible receivership. That happens when people throw up their hands and don't volunteer to serve on the board. Without a board to oversee the association's operations, you'd have to get a judge to appoint a receiver to oversee the association.
The receiver only answers to the court and homeowners wouldn't have any say in how the community is run.

Assessments would go sky high because you'd have to pay routine expenses, fund reserves and pay the court costs and receiver's fee (which could start at $200 a day) You think no one would buy the houses because they're made of stucco - what do you think will happen when potential buyers find out the homeowners don't even have a say in how their community is run?

I know all this seems daunting, but as long as you own a home in this community, you have to pay attention to your investment. That may be the hook you need to get people to pay attention - either deal with this now so you can sell the home at a decent price or continue to do nothing. Suing the board will accomplish nothing because there's no money and everyone will get screwed.

It's ok to prioritize what needs to be done first, but then you have to buckle down and do what's necessary. I also recommend you go to the community association institute website and invest in some of its educational materials. they cover a variety of subjects for new and experienced board members and homeowners, ranging from reserve studies to efficient ways of running the board of directors. A HOA is a non-profit, but it must be run as a business. Your community's days of running it like a casual block club have to end. Good luck!

This is likely synthetic stucco - well documented problems with early adopters. Lots of historical material, lessons learned, etc.

Where are your Bylaws?

Yep - you will need to organize the community to change docs to allow siding, or redo of synthetic stucco using new techniques. I think cementious products are probably better than wood, but that can be left to homeowners. Perhaps find a reputable siding company that will price all the houses based on size, etc ...see what kind of price en masse.

Get more opinions wrt the tress ... wait and see what happens.

Focus on comps and the stucco issue ... changing your CCRs will keep you busy.

Hello - thank you everyone who responded.

I'm working with an attorney now to figure our mess out. We do not have any bylaws - nothing was sent to the recorder of deeds here in PA and the HOA insists there are none. Just the Declarations which do have some very basic rules but zero operating procedures. Our board is holding an election tomorrow, and yes I'm running for a seat. Hopefully we will get some new folks and we can start to develop a plan of attack.

$7k reserves isn't low, that's a full blown emergency. Nobody in their right mind would buy a property in an HOA with reserves that low. I'm the HOA president of a 15 unit condo building, and we're deeply concerned that we're down to $50k, and our fees are range from $350 to $600 per month per unit. You are going to have to get everyone engaged. Offer payment plans if you need to, but you'll need to get the owners to realize that they chose to purchase a home in an HOA, so if you need to raise funds, they'll be responsible for it. You won't be doing anyone any favors by trying to wish this situation away. You need to do what's best for the HOA, and if the owners don't like it, they're free to leave.