I'm located in the SF Bay Area in San Jose, so if there's anyone I can buy a coffee in exchange for some of your time, I'd be more than happy to connect.Lastly, I don't think I'll be ready to start seriously looking for a first investment for a few months, so the question is, when is the right time to start talking to people like real estate agents, brokers, lenders etc.?

Connecting with a lender that can run numbers for projected mortgage payment vs  market rents in relation to the area you're looking into would be a good first step! 

I've been wanting to raise capital but its not easy finding lenders.

However, the lender that I utilize for that with my clients has not sourced funds from their account, so a personal loan or funding otherwise is still possible to bridge the gap.

That said, each individual lender will vary slightly in HOW they underwrite expenses for your DSCR, so it's very important to ask each potential lender about their process.

will lender consider actual rent roll or will they be using market rates? 

TIAI would run this by a traditional lender as well as have your attorney review the bond for deed agreement.

Hi Jesse,As a lender, I am seeing more borrowers getting into multi-family due to the higher rate environment and challenges with cash flow.

Consult a mortgage lender with experience in FHA loans to learn more about your financing alternatives and obtain a preapproval.Implement Your House Hacking Strategy: After locating a suitable property and obtaining funding, carry out your house hacking strategy.

Anecdotally, I know a lender who has funded several flips that have turned into STRs and he says his client is doing very, very well which actually surprised me.