I gained a little bit of social confidence, probably after about 8 months to a year (this was never a fast process, nor was it ever deliberate). 

I am currently saving up 20% for a conventional loan (as it may not be possible to owner occupy) and my biggest concerns at this point (along with all the other newbie concerns) is that one of my recognizable weakness is home improvement.

Being in SoCal, I can confidently bank on eventual appreciation.

Possible properties to tap areSFH worth about $330k, current mortgage 141kSFH worth about $270k, current mortgage 128kDuplex worth about 375k, current mortgage 184kPurchase price of new property is approximately 1 million, so I need to come up with $250k-$300k.I'd prefer not to sell any current holdings because they're located in transitioning neighborhoods that look to improve a lot in the future.I could do cash out refinancing, but that's a long process.

Maybe 1 or 2 houses fully paid off will give her an income that will improve her quality of life without having a major debt.How much time does she want to invest each day/week/month? 

Just let them know you haven't done improvements yet, so not interested in drawn out appraisal process. 

I would position it (diplomatically) that you work hard on your business to help improve the neighborhood and pay your share of municipal taxes, and you just want a reciprocation of that investment to repair the "city's property." 

If you have a local REALTOR you can contact there is a feature in RPR that will take an improvement on a home and consider the area and it will let you know if it will help the resell.

Obviously it depends on the property, so some areas I’m thinking can be improved are window replacements, exterior painting or interior painting.

I am not interested in being a lender, I like owning real estate, improving properties, etc.