There are companies already specializing in this you should try to find. 

According to the statute it needs to be a separate account set up and specially labeled as a trust account.

I am CPA that specializes I real estate and international tax.

Yes there’s lots of unlocked potential with travelers specially in renting to them during their contracts.

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

@Kenneth JesterI have an awesome attorney in Annapolis who specializes in real estate who also invests in real estate

I would prioritize finding an accountant who specializes in real estate taxation over one that is local.There are 20+ accountants on this message board who specialize in real estate taxation.

I'm assuming during these tough times I don't believe banks would still manage to be greedy at this moment. but who knowsQuestion 2) When scoping out the property, I noticed on the website it had the tag "SPECIAL SERVICING CONDITIONS APPLY" I did check bigger pockets but I don't think I understand can someone please explain this?

I can't say for sure since it seems like there's some info missing here, but it looks like your tax pro doesn't understand what a short term rental is.I think it would be worth it to pay for a consult with a tax pro who specializes in real estate and have them look this over. 

My opinion:  The only way working as an appraiser will give you more knowledge for your flipping business is if you target appraisal companies that work for lenders that specialize in construction loans and use appraisers/inspectors to inspect & approve work for a borrower to receive the next draw.