I wouldn't have to pay capital gains because I lived there.The main house has two separate apartments and a tiny house out back.

Only one bath in the house, so I'm not sure I want to cheat it, but the br is tiny and currently has no closet.

I DO actively do a lot for our rental (pool maint every week, fixing every lil tiny thing every week, etc...).

After thinking about it for a little bit, it makes sense to assign the rental agreement IF i was also assigning my option to buy, but its still unclear.I was hoping someone could help me figure this out, or even better, point me to a good source of information that goes over the tiny little details of LO sandwich paperwork and how settlement works with them.1) Is it necessary to assign a lease even if i was doing a double closing?

THAT is a perfect comp (it was a tiny bit smaller).  

@Ramon Purifoy I would love to invest in real estate where I have family as well, because then I know I could trust them, but my family is from a tiny town in the middle of nowhere and my wife's family is from San Jose, where it is too expensive for me to invest.

A tiny basement studio with no light and old fixtures ... probably not going to do it.

CIREIA, INREIA, and the Alpine meetup are all great meetings!  

I like the idea of it, because it's only 1.5 Hours to Washington D.C. etc and would love to build either a cabin, or something low maintenance like a Tiny House to rent out and/or enjoy for myself. 

I put in an offer of $170 and they accepted. 9 apartments rented at $350 one is tiny and rented at $200.