I liked the tenant, school is starting back etc, I told them they could pay first month and security deposit and I would let them have the rest of August for free.

You can start to educate yourself on the individual components; how much does it cost to paint on a per sqft basis or what is an average kitchen remodel.  

8 in 24 months is no joke, especially chipping away one at a time, I'm sure it has come with plenty of teachable moments, but its awesome that you are able to ask the question of how to scale.To start, a hard money lender that is only allowing you to do one at a time with your track record is... well... kind of silly.

So, if you start with a duplex, your next purchase could be a triplex or fourplex.

I am well versed in pretty much every facet of Real Estate: house hack, LTR/MTR/STR, multifamily, and fix and flips primarily.Aside from that I am also (somewhat) a serial entrepreneur, having started and sold multiple business' over the last 15 years.I also meet with 20+ professionals every week, through referral groups, meetups, and just 1 on 1 sessions trying to get to know people and make connections.I would love to chat with you if you are looking to meet people and get more information about real estate in San Diego!

Minimum loan amounts vary, but the product we work with most often starts at $500,000.

Just to be clear, I would only charge them for lost rent, from the date they were to move in until the date someone else started paying rent.Now, would that hold up in court?

I'm now aware of any "lifetime" limits for FHA loans, but you're required to live in the property for at least 1 year after the loan starts.

Talking with my partner, we started to talk think through worst case scenarios & options we’d have if it doesn’t get rented in several months. 

-Start with a JV structure on a few smaller projects to establish a track record before seeking full financing on your own.