Hi there,I’ve been using Buildium for the past 8 years and have had a great experience with it.

Glad you have experience investing locally. 

Quote from @Drew Mullin: I have some experience in the south Florida area.

Just to name a few: Borrower's Experience FICO Loan Amount Loan Type being sought: Perm (30 yr ams), Bridge (12-36mo I/O), Rehab (12-36mo I/O), Ground Up (12-60mo I/O) Property Type (1-4 unit, 5+ MF, Warehouse/industrial, Hospitality etc)If you have a specific deal in mind, then you can have a lender (or broker) look at it and give you a better idea.

Based on my 20+ years of real estate experience, I’d say renting the condo might not be the best option—$2,000/month rent minus $800 in condo fees leaves you with just $1,200 before taxes and maintenance, and seniors' condos can be tricky to rent.

I'd connect with some local investors either through the Airbnb app.. can message them as a guest and ask for a phone call to see their experiences and see if someone can send you their P/L or share experiences, and or connect with local facebook groups.

Something that would be a cool experience.

I was wondering if anyone here has purchased properties from him before and what were their experience? 

I would try to find an agent with investor experience and, ideally, a focus on investment properties. 

@Amanda Lindsay Which property management software did you end up going with and how is your experience?