As the market improves, you might also have a chance to refinance and lower your payments.

We improve the kitchen and the patio but just because we live here.

The refi or additional debt of any kind will impact the current performance of your property I'm never a great fan of selling a good producing property - unless I am certain I can improve the overall performance of my portfolio. 

Marina improvements ahead of us, county jurisdiction liberties on STRs, and an upcoming golf course has really made this area go nuts!

Then focus on improving your interviewing skills to help you build a solid team on the ground wherever you do choose to invest.

Any improvements that were done over the years had to be done to code of that year . 

This second property is in a MUCH improved neighborhood, which draws in a better class of tenant, it's professionally managed by a trusted company, and it's structurally sound with recent major improvements.WHAT'S NEXT??

Sure there were communication challenges and that’s where I stated they and their affiliates can improve on.

Shortly after Roofstock acquired them I have seen improvements and haven't had issues with bank account connectivity.  

For an unrenovated 1+Den/1BA LTR in our section of Northeast though, $1,300-1,400/month is certainly in the ballpark of what I could comfortably get with some very minor improvements to the space between tenants.So all that being said, I think your target of $1,500-1,600/month for your 2BR units would be more than doable.