Perhaps this isn't the best way to measure the value of the property.I will keep your advice in mind and continue to think about whether there's a way to utilize the land or if it's best to leave it as it is for now.

The extensive root systems will start caving once removed, which will cause issues for a while -- we had one down in a storm and we're still filling in where roots all over the yard continue decomposing, causing depressions in the yard even 5 years later. 

If you are trying to do them yourself and continuously fall behind, it might be a good idea to look into hiring a bookkeeper.

Being leveraged for a bit isn't the end of the world - there are usually options available if push comes to shove - 401k loan, personal loan, sell stocks, credit card (then balance transfer continuously until you can pay the balance off) and lastly sell.

He noted how he continues to prefer floating rate debt.  

What's this okole' talking abbout?

Nonetheless, the properties continue to sell! 

Second, it has continual sync issues with my various banks, so I spend many long and tedious hours reconciling my statements looking for missing transactions.

Hello, I am a 25 year old living in NH who recently started talking about purchasing a multifamily home with my partner.

Our project is similar to that larger-scale ADU project you are talking about.