In-unit washer/dryer is always a plus people are willing to pay more for, but even it's just on site and not necessarily in their unit it will perform better than a space with no access to laundry. 

When I do it for me and my clients, we go very conservative to give better expectations of the transition process, than if it goes better, great!

This also leads owners to ASSUME simpler is better when it comes to management contracts.

Or is it better to transfer the property to a trust owned by my parents where I will be the beneficiary? 

If it will take you 2 to 3 years, and you can refinance this before you break even, you are better off planning to do a refinance and save your money on the buy down. 

Anytime Mailbox is one of the better national ones!

@Philip Jones we've helped our clients do over a hundred.As some of the lenders posting have pointed out, the challenges are:1) Property value and corresponding loan size2) Appraisals have much better comparables than 5 years ago, but may still be an issue.3) Property condition can be an issue via the appraisal4) Ownership seasoning - most lenders looking for 6+ months or incredible documentation for cost of improvements made.5) Most DSR lenders require professional property management.Always try a small local bank or credit union, but most will expect you to transfer your business bank accounts over to them. 

Sarasota STRs are OK but there's a few reasons I'd recommend going with Pinellas county over Sarasota other than the raw numbers being better.

But this also helps me feel better I don’t have an HOA where I’m renting.

I'm always looking for some automation tools (I would be happy with basics like email management), but I definitely needed some resources to better understand it all.