Your life style has lead you to this situation and you must change your lifestyle in order to be successful with real estate. 

We see it all the time with the conversations on what cars/vehicles folks drive :) here in BP there is a badge of honor to drive a 20 year old 250k mile car/truck :) Myself I saw my dad do some of this although he never got to the utra wealthy stage by a long shot but made good money in RE however it was not until he bought old style timeshare in Maui that he would finally take a vacation..

If the area can support new construction, determine the best style, size, and type of new build for that area.3.

On the advice of the fireplace guy who did our last cleaning/inspection, we sanded down the brick inside and painted it with the high heat black paint, and it states in the lease that they may use a fireplace-style candelabra if they'd like, but any other use will trigger all the rules in the Fireplace Addendum.   

I really like the investment style you brought up, but c'mon Curt, if you're going to invest you should use your HELOC to buy the Yankees or Disney World! 

The rental had ratty furniture, a record player prominently featured in the marketing but it had no speakers, missing basics items in the kitchen, lots of drunks in the concrete hallways that reverberated right into the bedroom at 2am, a strong odor of urine outside, and more.We have super hosts in this forum that have hundreds of 5-star reviews and are masters of the craft, but I look at their rentals and see they don't have any artwork on the walls, decor is basic, they do nothing to make the guest feel welcome, etc. 

Location. 25 minutes to beach, 40 minutes to Florence, 15 minutes to Pisa, 60 miles to snow skiing.  10 minutes to Home Depot style store, etc.  

I work with a lot of MTR investors and what I am seeing frequently with multifamily acquisitions, particularly with new investors, is that they often test the property just like you're mentioning, as a way to dip their toes in the water and see what works in their area and for their personal style.

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

@Mike Gi be sure to check Airbnb longer stays and Furnished Finder to see what your competition's pricing and decor are like and make your properties pet friendly if you can as this is always a way to out compete the competition.