Buying two rentals in one year can be a challenge, but there are creative ways to make it happen:House Hack the Duplex: Buy the owner-occupied duplex first.

Gross rent multiplier (GRM) A method that divides the purchase price by the gross annual rents when the property is 100% occupied.

Either way, model prospective deals to maximum stress test and to see if it cashflows after you move out and fully occupied. 

Honestly, I've given up on finding cashflow anywhere close to the city due to rates and prices, BUT some other opportunities you may want to consider are:Live in flip - mentioned earlier in this thread, always a solid option in any market.Condo conversions - good money to be made from this and since they're a little trickier than a traditional flip there tends to be more inventory available that would allow for a profit.ADUs - come February 2nd, ADUs are allowed BY RIGHT on any SF property in the state, owner occupied or not.

There are 9 x buyers for owner occupied houses than there are investor buyers. 

Basically - I want a PM who keeps the property in good shape and occupied to get paid, and a PM who is either bad at maintaining properties and finding good tenants, or just really unlucky, to not get paid.- PM charges 8% of rent, which escalates to 10% if the property exceeds 95% occupancy with rent collection. - PM charges minimal fees.- PM is contractually obligated to perform annual maintenance/inspection to keep property in top shape. - PM provides a cash based accounting report every month, for every unit under management, that clearly labels all rent, all expenses, including management fees, and the net directly ties to the amount of money deposited into my bank account.- PM is a licensed handyman, or has them on staff, and takes care of most unit turn work at a reasonable rate. - PM has no breakup/termination fee- PM does not take project management fees, except on large or complicated CapEx projects exceeding $5,000. 

Quote from @AJ Satcher: I am currently house hacking with an upper/lower setup - I occupy the upper.

You visit occupied properties?

If anyone has an end lender that has successfully closed a handful occupied padsplit loans and can underwrite based off actual padsplit rents I would really appreciate an intro.

Not sure about MTRs.My general conclusion was that it is tough to do business in the town if your goal is to buy property as pure rentals out the gates and no intention to occupy.