Now you see how expensive dining and living rooms are that could be converted. 

   - convert new RE purchase to STR.  

I am going to talk to my CPA and see if I can convert.   

Just a quick comment and recommendation about Roth conversion: Never convert cash into Roth; if you do - 100% of the cash converted is taxable.

You could also sell it to rent to own, take a downpayment from it, and keep title open until the pay their part and re-assume title if they cannot convert.

There are many reasons that adding a single ADU in southern CA is a less than ideal RE investment (i will post a list at the end) but the negative initial equity is a primary reason as the initial negative equity position consumes the initial cash flow and can take many years to recover.As for converting your home to a rental….

query=garage#sear...If you can rent a 2 garage at $450 without spending ~$150k for a garage ADU conversion, no work/risk of the ADU conversion, the lower maintenance/capex, easier eviction, no rent control, less tenant interaction, it will not convert your SFR to rent control, etc, it seems superior to the garage ADU conversion.  

Since you are already familiar with house hacking, I would consider converting your current home into a rent-by-room or whatever it takes to keep it as a long-term rental, then look for another home you can hack.

If you can find a place where the HOA or COA is flexible and you are able to convince the membership to go into development and perhaps convert the property into a co-op you could build a new apartment complex with commercial rental spaces on the ground floor and residential spaces on the top. 

With a large portion of the incoming migration coming from international residents moving to the District, emphasizing improving and bringing back Washington D.C. sports teams to the city should create a strong desire for domestic residents to want to live near a fun, community engaging activity that is very relevant to those that live in and around the city.The District also has other programs it is running to make the District more attractive to live in outside of just working in the area, such as the Office to Anything program (Source) and the Housing in Downtown program (Source) which will incentivize developer through tax credits to convert office buildings into new construction housing and new construction retail properties, which should continue to attract more residents back to the area.D.C. also understands that with all of these big changes we have seen, the strategy and allocation of resources from the government moving forward should be reassessed to create a city that is adapting to the future trends to remain a safe and desirable place for residents to live.