I’m inclined to hire a property management company, but still considering all options.Problem is - the property is UNIQUE.

It also requires gaining a level of sophistication and knowledge that not everyone has the time, inclination or ability to do.

It also requires gaining a level of sophistication and knowledge that not everyone has the time, inclination or ability to do.

.: *assumes CA averages for valuation, rent, profitability, etThere are strategies for starting small or starting big, that are discussed but I am not entirely sure what would be like too big for a first deal...My inclination is to assume that the larger the asset or more units the better, as there is less tenant risk, professional property manager, etc.

It would be our preference to invest in upstate NY because we could drive there relatively easily, but if there are better deals elsewhere, we would be more inclined to go with option (1). 

Place I am looking at has been operating as a STR for years and seller says no license required, but not inclined to take his word for it.

If you are inclined to go down the DST route, I would highly recommend going with a RIA who can help save you on fees and provide true due diligence analysis.

Likely we'll be able to purchase in the future even if they aren't inclined to participate.That sounds like a solid JV structure, leveraging the land as equity really does make it a win-win.

Given my inclination to keep the rental property, what are the potential benefits or drawbacks of using a HELOC on this property to finance another investment property?

If you want to offer a "rebate" of some kind after they stay up to date for certain amount of time, I'm more inclined to go that way, but in general theres no real good reason to put yourself as the owner in the middle of the utilities unless they aren't metered in a way to bill directly.