What is the best way to finance another property, or current debt to income is too high for conventional.  

Go conventional if you can for the best rate/terms. 

Usually local banks only, usually conventional unless you have a different kind of business model from strict BRRRR.

@Aaron Garbade let me shed some clarity for you...Conventional max financing: 15% down for a 2-unit, 20% down for a 3-4 unitConventional max loan amount in Tampa: 2-unit $702,000, 3-unit $848,500, 4-unit $1,054,500FHA max financing: 3.5% down for 2-4 unitFHA max loan amount in Tampa: 2-unit $456,275, 3-unit $551,500, 4-unit $685,400The max loan limits will be increasing SIGNIFICANTLY for 2022, if you're not in a hurry.Best of luck!

Should I still try to write multiple offers with different types of financing options for a better likelihood of getting under contract or should I just go with full price, 21 day close conventional financing like my Realtor recommends?

It's a bit higher than most conventional loans, but it also doesn't go on your credit report and the loan can go as a LLC for liability protection. 

Hey Gabe,You wouldn’t finance it with an LLC with conventional financing.

Most lenders are going to require 20% down on a Jumbo second home.  10% down is allowed on a loan that is within the conventional loan limits.

There isn't any conventional lenders that will do a new mortgage with a forbearance that hasn't been repaid yet. 

Because of this estimated payment my debt to income ratio isn’t working out to push the conventional loan through.