Chances are attorney's fees will outweigh the collected balance.

As you continue with your real estate, the tax savings with a tax planning accountant will far outweigh the cost, not to mention eliminate the headache of trying to prepare your own taxes.

In the first analysis which included house hacking, the expenses far outweigh the cash flow and would result in me paying almost $600/mo for the mortgage and other expenses.

The risk out weighs weighs the upside in the next couple of years. 

Because if it's just a few, then the dues and fees will likely outweigh the savings in getting it.

Should I set up the rental in a business right away or do the overall business costs/effort outweigh gains with one unit?

Overall, I've found the benefits to outweigh the cons, but you'll need to assess your own situation.

The lessons you learn will far outweigh these “minor” differences in the long term.

Cost to me was outweighing the benefit. 

There are rare situations in which we can do properties under $200k, otherwise, the cost of an engineering-based method of cost segregation, the IRS' preferred methodology, outweighs the advantages of doing a study.