I recommend to my investor clients to make sure the property would still work as a long term rental in case additional restrictions are put in place against STRs.

Do I move forward with them filling out the application before I've even closed on the property, along with paying for the credit/criminal/background check and sending them the Estoppel Certificate?

I'm in need of additional funds to pay off lawyer fees and my wife's interest in other properties. 

Additionally, as I embark on this journey towards becoming a licensed real estate agent, I'm eager to gather tips and advice from seasoned professionals.

I would add in addition to square footage and sleeping capacity look at similar amenities.If everyone in your area has a hot tub , then you need one too.

Please reach out if you need additional info. 

Credit Unions?

We then have an umbrella policy for additional coverage and I add damage protection to all of my reservations for additional coverage. 

These specific loans allow me to assume/get her off the deed and the loan without a refinance (it's an amazing loan through Mountain America Credit Union) The CG is calculated into the appraised value. 

I'm addition to what's already been  said remember you have no control over the HOA regime fees.