. - Be careful not to let the "tax tail" wag the dog.

@Andy OkamotoOne cautionary note: if your idea of "cash flow" is $10K in net operating income, $120K before taxes in your pocket every year off your rental property, well, if it happens to you in 10 years, it will be a low-probability event with a lot of lucky breaks and eventually will likely ruin your life when you make a misstep because you assumed your lucky break was the norm.If you're serious about moving out here, at least look at the Pittsburgh area and its proximity to Carnegie Mellon (tech) and UPMC (health care).

This year I have also hired a bookkeeper at $50/hour to take care of the rental aspect of the financials.

I’m weighing the pros and cons carefully and considering my options.

But about service based businesses, you're referring to something like a lawn care or pet sitting type of thing?

I am familiar with the "rudeness" but that unfortunately is not so uncommon when dealing with government employees who have to deal with the public on a daily basis and is something you just have to have thick skin for.

I have a bottom line amount I want to get and don't really care how I get there which is why I thought there might be some options.....

My company treats this activity the same (well, almost) as a Child Care (Day care) center, which is a commercial and licensed activity and not appropriate for our leases of single family homes.

(They shouldn’t care since they won’t be there anyway.

If you prefer to have the MMLLC involved from the start, consider a "drop and swap" strategy, where the property is moved into an LLC before the exchange, though this requires careful timing.