While I love the idea of eventually owning a paid-off primary residence, I’m debating whether it’s smarter to sell our current house and use the equity as a down payment on the new home or to keep it as a rental.

great idea.

That way the lender has an idea what it is you are doing and cost.

You should find out what percentage of the rent is being paid by S8 and by the tenant.Tenants have to sign the rent increase and some won't because they don't want their payment portion increasing.It's also highly unlikely a S8 office will approve the huge increase from $797 to $1300.- BTW: the $1300 includes all utilities being paid by the landlord.

It is a goofy idea but it is currently being explored.

I wouldn't let the idea of purchasing a home that has oil heat deter you. 

A VA can help you compile lists of potential wholesalers, manage follow-ups, and even track responses from your marketing efforts—freeing you up to focus on high-level strategy and deal analysis.Hope these ideas help!

I started this a little over 3 years ago now.I think thorough research, and data will help make educated decisions, and the real winner in this market is finding a mix of at least 2 of the four:  Off market discount, fixer upper, lowball on market offer, or seller financed/subto.Also if you are planning to do it in a populated area I also think its good to take on the idea of not cash flowing for a few years, and also considering air bnb if you want to reduce costs even more.

If you track listings a full lap around the calendar, you get a real idea of the revenue comps in an area.

My idea is to 1031 the SoCal property into the in-laws farm and rent back to them for a minimum of two years, and then decide if we keep renting it to my in-laws, or move my family into it.