You may find better luck/options with local banks/CUs or even private money in the subject property's market area, but with nationwide institutional lenders, you will find that most (if not all) have no appetite for them.

I didnt' find anywhere in your post where you indicate the lending institution, but I will say, a lot of lenders (mostly banks or credit unions) will "overlay" standard guidelines. what that means is that they will impose more stringent guidelines above and beyond the standards.

I have an investment property (MA) with a good amount of equity, here's the math:$385 Purchase Price - Value $570 - I want to flip it to a multi in Philly. 

Hey Alecia thank you for the reply 🙂 will defiantly try my luck with local financial institutions in my area.

The city is home to many Fortune 500 companie, growing population, and it still remains an affordable housing market, especially compared to Massachusetts.

Are there specific lenders or financial institutions that you recommend for beginners?

as far as having a lender in the state you want to buy in, i don't personally think that matters, as long as you know right away whether or not they can lend in that state (many investor-popular lenders that i've talked to can't lend in MA, which is where i live). 

I live in Massachusetts and hear that it could be quite a good investment to buy a property in Florida and AirBnB it out. 

If his credit capacity is sufficient, and his experience sufficient, he may be able to obtain a loan from institutional sources to compliment whatever capital he’s personally able and willing to contribute.  

I wouldn’t be surprised, with increasing rates, that lender will re-institute a policy of using an increased “qualifying rate” rather than the “actual rate” on a heloc for loan qualifying.Bottom line for investment prospects is that it is easier to qualify for a future loans by consolidating all non-mortgage debt and using your cash for down payment to secure financing for your next real estate acquisition.