It's highly unlikely that you'll get a DSCR loan without a PG at this point.

I'm a mortgage broker that does residential and investment property loans in Florida- happy to connect. 

Are there loans that I can take out against the entire 10 property portfolio, or do people usually get a single loan per property?

I just need a little extra help with the next steps and figuring out all of the details needed to make it happen.I would like to close on a deal by the end of this year, using either my VA loan or an FHA loan to house hack.

Should we leave her conventional loan and take out a HELOC?

Megan, Not sure if I can help you exactly, but a few items that might help: 1) As you are out having conversations with potential private money lenders, you can start the conversation about "Did you know you can use IRA, or old employer 401k funds to make private money loans, secured by real estate?"

Did you purchase it with a conventional loan or DSCR?

-Got lenders who do DSCR loans?

I will be making around $110,000 annually and have $20,000 in student loan debt. 

Get a few quotes. and if you do not do it, when you go to refinance into a long term loan the appraiser will likely mark the report as "subject to" a structural engineer report of the foundation. and you will not be able to refi until you have done the  work that is required.