From a tax perspective, If you want to Buy and Hold, you can just create an LLC. 

Look up the areas calendars for special events and create block out dates.

Here in Cleveland just like the rest of the country we have many neighborhoods with homes priced well about $300,000.I created The Ultimate Guide to Grading Cleveland Neighborhoods to give out of state investors like yourself an idea of what's what in our market.

Of course, technology has been created, and will continue to be created, that will make home buyers' quest for property easier if they choose to go-it-alone, but the fact is, the technology that we have today provides insight that is far too generic to be considered "valuable" in my opinion.It all comes down to 2 things for me:1.

DO NOT have a combined version or you may regret it.If all else fails and you cannot find these at a document shop near you then search for a "real estate laywer" and they SHOULD be able to create these at an insane price.

That would allow you to access some of the equity you've created for yourself without selling.I'm actually in a similar situation as you. 

I have found that the Waianae coast offers some good values still, but most people shy away from that area, which in my opinion creates potential opportunity, but also risk.

I live in Florida now, I wish Austin had a beach :)Reduce Cap Gains: The only option you really have if you already sold the propertyis invest or create your own Opportunity Zone LLC.See the Austin Map for the areas you can invest in while paying no cap gains :)Full map here: https://esrimedia.maps.arcgis.com/apps/View/index....

I also feel like as these coach houses get torn down more and more for new construction there will be less and less of them which may create a rarity/premium from a long term buy and hold standpoint. 

I'm planning to have a structural engineer to create architectural as-built floor plans for a 2 story mixed use building I own in California.