@Rocco Swinney I wish it was more creative, but I just did a traditional commercial loan with a local community bank that was a referral from the selling broker.

Traditional banks with Fannie / Freddie / conventional loan types will sometimes push back on the LLC issue, but there is a BIG world of funding and lending for investors outside of that box.  

If those other things are more important that a little bit of interest rate, you could look at non-traditional private lenders. 

When COVID hit and we were not allowed to show property traditionally we changed to an application first model. 

The potential cash flow from STRs is great, but I would encourage you to run the numbers as a traditional long-term rental in case the short-term option doesn't work out.Are you planning to do another house-hack on the new property, or will it be exclusively a STR?

They could be offering bad advice without even knowing it.If you expect the place to be vacant for more than 30 days most traditional policies will not work.

What problems might we encounter when using conventional/ traditional financing more than one property at a time and what type of mortgage rates should I be anticipating?

He specializes in traditional financing and is an incredible guy!

Paying a buyer's agent 3% is far more palatable to me than the traditional alternative.

If you get a full time job out of college with a contracted salaries you can most likely buy an investment property through traditional financing.