I own 2 small LTRs and want to wholesale to earn some capital so I can start flipping and STRs. 

I have been been on the fence about what area to start this journey, I live in San Jose California.

Check out some local meetup groups in your area and start learning.Good Investing... 

It's also an old city with some geographic constraints to new development...if you're close to public transit in a good location, there's always going to be upward pressure on price (and rents) and limited supply. 

To be honest am unsure where to start after buying raw commercial land.

Although 5k is a great start, the Airbnb market is very competitive and you will need more set aside in order to properly acquire an investment property.

Smaller multi-family is significantly more common in the Northeast, Midwest, and Western cities who had their economic boom in the roaring 1920s-60s and thus, tons of high density zoning was developed across the country (but not the South).

Unfortunately, I do not have experience in this space; therefore, I hope to get guidance from an experienced NYC developer.  

My target purchase price is under $1.7M and prefer cosmetic fix to start with.

I started with an afternoon every other week, which was changed to an afternoon every week.So I put issues into 3 buckets: emergency (a pipe is leaking), within 24 hours (toilet running), and non-pressing (a door is not closing on its own), which is where most things landed and are handled that way.