I've spent probably 200 hours now, studying the blockchain/crypto space.

But then have to go back and access it every time work needs to be done at any house?

Due to peaks in the roof, square footage is difficult to measure, but I believe it to be over 100 sq ft at areas with the ceiling over 7 feet.It is currently unconditioned space, so I was thinking of adding baseboard heaters. 

Join your local REIA and get access to other lenders, or join Illinois REIA online.

I also have access to Buildium through my PM, so I can see not only who has paid before those rents are kicked over to me, but I can see any repairs done during the month as well as as print out any P&L statements for each property.  

If the $1000 includes Open House signs, 3 months monthly fee, business cards, website, key access, a lockbox, training program so on and so on, then I can see why.

Then I became a pro member mostly to gain access to the BP calculator's (if you attend a webinar you might receive a discount code for the pro membership at the end).

If space is a limiting factor you could look into a sand mount to replace a leach field, but again, ask a local expert.

The commercial space is occupied currently, but the two apartments above are vacant and need a complete rehab.

For example, a vacation condo rental that is treated as a trade or business for passive activity purposes solely because the average rental period is seven days or less is still a real estate rental exempt from the self-employment tax.Per Reg 1.1402(a) - 4(c)(2)- If only services provided in connection with 7 days or less or 30 days or less are beyond customarily provided in connection with the rental of the room or other space the activity produces SE income, if not, NO SE taxes.