Purchasing an investment property increases the level of difficulty of your tax return.Purchasing a house-hack is even more difficult.To make it even more difficult - you plan to make improvements so you have to determine which costs are currently expensed and which are capitalized.Not only have you acquired an investment property but you also acquired a personal residence.As a result, direct expenses towards your investment property and indirect expenses are deductible business expenses that can be used to decrease your net income from rental activities.With all that is said - you are trying to operate a business so I would hire professionals to help you with your tasks.

The contractor must be FHA qualified and will be paid in installments (called draws) when certain levels of completion are achieved.

It was also a bit of a fixer-upper and I knew that I could increase equity on it that way. 

As mentioned, you might be able to drop some road base and raise the level of part of the property to raise it up out of the flood plain. 

I would ask your CPA at what level he/she thinks S Corps make sense. 

She quickly went to find someone else to talk to.Lots of folks renting out STRs these days are upset by the level of recent competition in the marketplace.

I would seriously sit down and look at "what is the minimum we can do to get this into a sell-able condition".Sell-able doesn't mean "looks great and tenants/buyers will love it", it means "a buyer will walk through and think, this can be rented at roughly market rent", and won't think, "man this is a fixer upper I'm gonna need to dump money into to make it rentable".Multis are, as I write this, still pretty hot.

I’ve done some surface level research and know that you can pay third-party services, but wondering if I can outright cancel due to medical reasons for my dad (cancer) who is too weak to travel.

I'd be most appreciative if those of you who are familiar with the area could give me some insights.First, the house is about 3000 square feet, and the plan is a total gut rehab with upper end finishings. 

I have a very good grasp of the real estate industry on a macro level and a fairly good grasp within a variety of sub topics within real estate.