You want an accountant who can help you strategize and who is responsive when you want to know the consequences of the financial decisions you are making throughout the year.Good luck.

But as someone who’s been in the trenches of real estate investing for almost 30 years, I continue to see some flaws.Some of the flaws I have witnessed are when tech-driven companies seem to lack backing from experienced underwriters or seasoned real estate professionals.

I have cash reserves and money in retirement accounts, but I don’t want to dip too deeply into my reserves.

Big players like Ford, GM, and even tech companies are betting on Detroit.

I would definitely look into seeing if there are any AirBNB arbitrage companies operating in the area that may be willing to take it on. 

We've always hired a tax protest company and have done so in three different states.

Gifting equity in a house may be more trouble than it is worth if you are not near the life-time exclusion1) Potentially having to get the property appraised everytime an equity is gifted2) Having a title company update the title every time3) Exemption of the gift tax return is normally for cash gifts below the annual gift tax exclusion, you may still need to file if you gift non-cash4) If there is partial ownership over several years, having to properly pro-rate certain items such as real estate taxes, mortgage interest and rental income if the property is a rentalBest of luck 

Since the previous owner is getting most of the proceeds does the closing attorney issue him a 1099S and then issue my company one for a much lower amount?

I have recently worked with a company that has an excellent offer.

No I would not go with a company charging that.