The management company replaced some of them, however there are still several other fees related to the theft that we are trying to get reimbursed for (they told us we would not be charged, they charged us anyways).

Any "perceived" deception at any point, will be severely counted against you by the court.

I am conflicted on whether to use the 500K on one big property (ideally multi-unit) or buy several smaller properties.

Quote from @Ryan Moyer: Quote from @Nick Velez: Hey Anthony,I have a few STR's in Gainesville and have lived here for about 7 years now and know several people with STR's as well.

I’ve been working with several lenders for DSCR loans, but I’ve found that the fees are quite high, with minimal benefit in terms of lowering my current interest rate.

I have several ideas.

If there are lease violations, mention them-you not having a key to access the unit WITH proper notice or in case of emergency is one of them.I'd also tell the tenant that they are clearly not happy there, so finding a new place is in their best interest as well and as they have several months, they should have lots of options.

I've worked with several loan servicers, and no matter who you use, it's not fun setting it up, but I've had easier success communicating with OnePoint.They have a login portal to track payments etc, like you mentioned. 

Between now and the time you retire, there will be a couple of severe recessions and likely serious inflation. 

I moved to Rent Manager (RM) several years ago and couldn't be happier about leaving QB.