In addition to Turbo Tenant, I would suggest that you have a local Realtor list it for rent. 

So ultimately we decided to suck it up and not take on the additional equity, which ultimately required us to take more time on completing the needed rehab, however in hindsight it was a good decision, because even just among our own family there's been lots of dispute on what we want for the business plan and personal STR useage....

There is the tactical "act" of underwriting, then there is the much more valuable "art" of underwriting.The act can easily be taught.  

Additionally, the funds they deposit might be significantly higher, and harder to recoup, hence they have the ability to close on a deal the lock up if they need to.Thats a good point.

Here's the deal: You don't need to withdraw and return the current security deposit just to collect the additional $100.

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

If you are looking to refinance the rate and aren't concerned with taking additional equity out on your property, then you should use a rate/term refinance.

You and your husband are definitely in the right place to get valuable information.

In our market it is important to make sure they are a licensed broker, carry adequate GL and worker's comp (and name you as additional insured).  

Since these accounts are in the business name, they don’t affect DTI, making it easier to secure additional funding.How fast you're looking to scale will determine the best approach—some investors go the business credit card stacking route for quick access to $150K+, while others secure business lines of credit for more flexibility.