If I did short/mid term rental I could do about $3.5K/ month for 10/12 months.

I am looking to grow the portfolio to short term rents in Daytona Beach, Florida.  

The short answer is No, you don't need it.

You can go the one property route but I think doing an agreement period is much more motivating for the agent (and will save you time, hassle, etc)

I have also utilized owner financing for longer periods of time, including personal residence and 2 barrier island houses on the coast of Florida.  

Although I’ve been investing in real estate, both directly and indirectly for 45+ years, I still get a “queasy” feeling when an investment does not perform as expected.My “aha” moment occurs when we reach the point when, despite the investment problems, we’re able to still show a good/substantial profit at the end of our holding period.  

Short of coming here and meeting face to face with them and come to a couple local REIA events to discuss, for those who are remote I would suggest getting into some of the NE Ohio REIA facebook groups to get some advice from locals.   

Once you have a short list, get an account with each one and run them through the wringer to see how they function.

The lot is flat and level, so we only need a short gravel driveway.

To list a few...Anyone who wants to increase their property’s income potential (and equity) and build new housing in a market that struggles with high prices, low supply, and few new construction.House hackers who live in their primary and want to airbnb an ADU love this strategy or vice versaInvestors who want to do both long term and short term benefit from having two separate units.Rental Restrictions on ADUs.Thankfully, Raleigh is very STR friendly and ADU friendly right now.