First off I'll say hilltop is a very large area.

The str will close before the land sells and then I would like to recast the loan to pay off a portion with the land proceeds.  

Property manager started off using my chosen vendors, but as the years have gone by (I left in 2015) some have dropped out and slowly I have just started using the property manager's vendors our of convenienve.

I have been using Reonomy for the past month and have found it very useful for identifying off market properties. 

Meaning if someone gives you $500k and you only are using $100k, you are still going to be paying some fees on the $400k because the lender needs to keep that cash on the sidelines.You are better off getting either DSCR loans for each or hard money at 12 months and interest only with extensions but realize that money will not be cheap. 

Hoa is very high, off the water and maintenance is starting to increase.

I will pay him off using another business credit line I have..key was that I  want to show that my down payment is not  borrowed money hence this plan

I told her the amount and he is an older man who lives off her social security check.

Ultimately, it's about ensuring the property remains attractive to tenants and maintains its market value without pouring money into upgrades that won't pay off.

It's usually pretty hard to try to piggyback off of what a previous owner may have done in the past.