The family dynamic isn't a major concern. 

Here’s another: majority of coaches/gurus have never even flipped a house .Years ago when I was just starting out.

Advertising a non-conforming unit without disclosing its illegal status could be considered deceptive (and fraudulent), opening the owner to major legal risks (fines or tenant lawsuits).Even private marketing, like word-of-mouth, doesn’t absolve the owner from liability if the unit fails to meet legal requirements.

I ask because I've interviewed a number of general contractors over the years for my various real estate projects and am shocked at how the vast majority showed up to the job site to give an estimate in a vehicle that did not display their contractor license number or business name.Aside from this one issue, they'd often have great portfolios, long list of successful permits I could verify they pulled, great references, no complaints on their license, and had been licensed for over a decade.

You think through the major systems in the house (roof, exterior or tuck pointing, hvac, plumbing, electrical, unit turns, common areas) and if they are all new you should be good for a few years (5-10). 

We've owned them for 20-plus years but the recent property tax increases have negatively impacted our cash flow as have major repairs such as roof replacements, AC units, etc.

I ended the offer to rent to the tenant on December 1st and didn't receive any communication from LMHA until December 15th when they tried to schedule the inspection...that's 45 days to process a voucher.We had another home pass inspection on November 5th and we hadn't "stopped and waited" for LMHA because it had never been a major issue before so we let the tenant move in...LMHA announced on November 15th that the tenant voucher needed to be re-evaluated by LMHA and that the rent rate needed to be adjusted (The story was the "Administrator A" reviewed and approved it but since they had resigned, now we had to wait for "Administrator B" to do it.

I haven't had any major issues, and customer support was quick to assist. 

All with 55% down.Generally speaking, a location that is near a National Park or major attraction(s) are going to be the better locations for STRs. 

This is actually one of the main reasons many agents and investors may not like them generally speaking (they are often not serious professionals with a proven track record of success, the vast majority are struggling to find their first deal and are time-wasters to interact with).