They will do the price shopping for you and find the based vendor based on your requirements. 

In fact, proposal #2 will require the home seller to go buy another home to live in (no tax credit for that, since it’s not their “first home.”)

I'll try to be helpful and concise here without being too long-winded...ESPP - Typically you buy this at a discount (Usually 15%) typically you get beneficial tax treatment on the discount and won't have to pay income tax on it as long as you hold it for their required holding period.

You may consider looking for seller's that will consider seller financing that may not require as large a downpayment. 

i.e. if you had a $190,000 hard money loan on House 1, you'd be able to get 80% LTV no problem with no seasoning requirements as rate-term refi

Along with the FHA loan, check out the loan from the Neighborhood Assistance Corporation of America (NACA).NACA was formed in 1988 and provides an affordable option for potential first-time buyers:✅ No down payment✅ No closing costs or fees✅ No mortgage insurance✅ No consideration of credit score✅ Below market fixed interest rateThere are several requirements to be eligible, starting with attending one of their workshops.https://www.naca.comI wish you all the best.

It also requires a small monthly payment, so once it's started we've got our impetus to meet at least once a month (lol).Speaking of which, I'd say it's nearing the time to propose another Yokohama area meet-up!

Sounds like I'll need to find that balance point between far enough ahead to not miss out on advance bookings, and late enough to use the algorithm boost to help as the season nears. 

Can transfering the title to a land trust help overcome the owner occupancy requirement on JADU

Some cities require the STR permit number in the title or very top of the OTA listing so city permit  technicians can scan and keep track otherwise the owner will be contacted and fined for forgetting or shut down if operating illegally.Some cities have a 24/7 STR hotline dedicated to receiving any complaints (from neighbors, HOA) for a code compliance officer to act onSome cities issue expensive fines for those operating without the STR permit