If you want to look at total expenses over the years, you need to look at total income received as well with your potential sale price. 

Well, not necessarily.

We have owned a STR in Florida's panhandle, which has done very well for us for 10 years. 

It can only be addressed in a one-on-one manner, because if you ask another CPA for a second opinion, it very well can be the opposite from the one you asked first.Here're a few of my personal pointers.1.

I think the house flows really well in person (open floorplan, high ceilings, large house with spacious room sizes) and you just can’t represent that in 2-D photosI’m honestly not sure how to do a video or 3D virtual walk-through or whatever, I haven’t looked into it and have no idea how much it costs.

While not necessary to be successful in RE going to college can be a fun experience prior to adulting and having a business degree is a well thought out safety net.

Your new place should turn into your new business location as well. 

(This includes character attacks as well.) 

I am looking to purchase real estate for both investment purpose as well as to offset as much tax liability as possible. 

Well done.