I was conducting an extremely seasonal business and after 8 years of operation the business was insolvent. 

@Jacob HavlovickBigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

Is the mid term rental business that you have a 'rental arbitrage' business?

This should bring up all of the homes in your area with pools.

If you are considering buying using Subject To - Subto, it's important to know what your exit strategy is.Talk to a mortgage broker (not a bank) and ask if that is a property you will be able to get financing on in the event you have to refinance quickly, because the Due On Sale clause was called.AndTalk to a real estate agent about how much you would have to bring to closing in the event you had to sell quickly.

I am not sure what type of real estate investing you're considering, but it sounds like, with your family and busy job, you won't have a lot of time to be hands-on or personally involved. 

That's just the nature of this business. 

Anyone in business takes risks, but a lawsuit and some other things don't look great.

Here is what the IRS says on the subject: Election for Husband and Wife Unincorporated Businesses A business owned and operated by the spouses through a limited liability company does not qualify for the election Only businesses that are owned and operated by spouses as co-owners (and not in the name of a state law entity) qualify for the election.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required).