These are usually safe investments as that's entry level home and has traditionally been not impacted by markets.

This is a type of capital gain taxed up to 25% at the federal level and not excludable under Sec 121.(5) If you rented the property before it was your residence, the math gets complicated.Make sure to confirm everything with your tax professional. 

Boston rents are sky high -- anything you can do to reduce your expenses (your living expense is your greatest expense right now, probably) go do it.

For example if you have a mom and pop tenant based on 17 bucks a foot rent because that is all their business model can support but a national tenant wants the site and can pay 22 because of location not only can rent potentially increase but also that new tenant value can be a massive difference.Mom and pop at 17 a foot and an 8 cap for instance.Say 4,000 sq ft box X 17 = 68,000   (8 cap) = 850,000National tenant at 22 a foot. 4,000 X 22  = 88,000  (6 cap) = about 1,470,000There are expenses involved getting the new tenant but value difference can be massive.Leasing brokers can perform a (void analysis) which not only looks at rent comps for box size but also what existing tenants are in the market,saturation levels, and what possible tenants optimally could go in that space.    

Also, make sure you have a home inspection as there are different levels of new construction. 

I’m very eager to learn more from the seasoned veterans as well as people on my level.

The goal here is to cut your losses and get back on level ground.

I am also a passive investor in a syndicated medical building.So I know the level of time committment involved with being an active real estate investor and I can compare that vs. being a lender or being a passive investor in a syndicated deal.Yes - being a lender is more passive.

I originally thought about putting a gravel parking area along the front/side of unit D back towards A as there is a curb cut for a drive and 2 units are lower level and the entrance is on that side of the building (cost would be about $5k range for it but would be more of a ). 

Obviously if you have to grade an area lower, your best bet is pull the stumps, but if you’re just trying to make clearing and level land, are you a fan of cutting low, then grinding or something the stumps?