I know nothing about wholesaling, but it sounds like to me you need to just pull a small trigger.

Your experience sounds like mine and many others.

We have considered new construction several times, but found it much more cost effective and a better ROI to improve existing buildings instead. 

This step up in basis effectively wipes out the deferred gains you referred to in your question.

@Aj Fortson It sounds like you may have already come up with your income generation plan:  taking over your dad's lawn business.  

It sounds like others have been happy with Stessa and Ren Redi so I'm going to check those out.

I have found many of their articles interesting and I am not in the medical field and have no idea how I ever even came across it years ago but do still read it when the topic sounds interesting to me.

Using the HELOC to pay cash for the property sounds like a good way to go and yes, the rents should help offset some of the debt for your DTI ratio. 

It sounds like you're working with corporate housing placements so are you signing the lease with individuals or with the company itself?

All you need is a few busy bodies who want to make trouble and you are effectively banned.In the Florida Keys, all but 2 of the islands allow STR for 28 days or more - how many folks can actually rent for a full month?