The insurer expects a baseline of maintenance and repairs, and you either keep up with them or you get dropped, and you do not want to get dropped in Florida.

Keep in mind it is a class A rental.I greatly appreciate the advice in advance! 

I keep an eye on the market, but will probably never take the leap.

Tenants paying rent by Venmo every month, which creates additional work to keep track of it all. 

Keep saving as much as you can.

I always like to have something that reels them in and gets them interested ( short term ), and something for the long haul to keep them happy.i.e, as you mentioned wave application fees, admin fees etc.

Keeping my fingers crossed. 

Rent Roll13. property survey14. prelim title report (your broker can help with that)I DO NOT Ask or recommend my clients ask for tax returns, credit reports, bank statements - These fall into financial privacy protections and if my buyer walks from the deal, there is too much liability & risk with having that information if were to be leaked.If a third party management company has been managing it, you'll get basic information (income/expense, rent roll & leases, maintenance records, capex (maybe if they oversaw)).Owner operated properties will have less of this information as most mom/pop operators don't keep good records, in my experience.Don't worry about all this BEFORE the offer. 

High income W-2 ($400k+) earner and would like to keep my job.2.

She does not sound like someone you want to keep long term.