But we are working on it and all of our partners are aware of this desired outcome and want to participate.

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.”)

It ultimately comes down to your budget and desired level of privacy in your living situation.

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.

Would it require you to change your lifestyle? 

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!

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