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). 

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.

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 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).   

Also, the home is located near the following: major freeway, hospitals and healthcare facilities, located within 15 mins of downtown, plenty of restaurant options nearby, etc.

He's a major hard money lender in town and has a fairly simple process to get quick funding.

I've been a RE developer for nearly 20 years with a majority of my work in the CA market.

If you’re tackling major work like a full bathroom gut, expect it to stretch out, but with a solid plan, you'll stay organized and avoid delays.