@Jon K.As always, your tax guy is in the best position to help you with this as he know s all of your facts and circumstances.

For example, some states you cannot give notice to vacate to a M2M tenant unless certain circumstances are present.

And fico is down the list at what my commercial banks look at for multi million dollar loans I get.. those are based on the 3 Cs  Character  Capacity Collateral   and of course experience and length of time with the institution.. now this is for my development and construction loans.. 

Multiply that by the complexity of each investor's individual circumstance and you get an infinite number of optimal strategies. 

I have the same ones for each state so 1 for OH, 1 for FL, etc.4.Keep piling cash up so that I have reserves and as a backstop should/when the economy tanks.5.Focus on developing a side gig/business in 2019 to increase my income snowball.6.Research ways in which I can re capture my down payments and closing costs which total $170,000. 7.Go out hunting again in 2020 but keep analyzing deals between now and then and if a REAL good opportunity comes up.

In prior years, you would test your business to determine if you were actually running (a very unsuccessful) business or if you were simply dabbling in a hobby.This article is a pretty decent break down of how that test is done using the facts and circumstances present in your endeavorIf running an unsuccessful business, your losses might be deductible, buy depending on the nature of those experiences, they might just be Start Up Expenses, which are handled much differently (and also not entirely deductible)If you are just dabbling in a hobby, then prior to 2018, there were special rules about writing off those expenses, but in 2018 most of the ability to write off Hobby Expenses are now gone.

Talk to your attorney- depending on circumstance an LLC may not necessarily be the best option for protection without the headache dependent upon what your goal is, your net worth is, property value ect. 

Residential condos are selling for $400+ sq ft. and no new builds will happen ever as town is surrounded by non-develop-able land.

You need to develop a pro forma and use that to come up with a return on your investment (whether that's cash on cash, internal rate of return, etc).

Alternatively, if you have a partner that you trust and fits the above criteria, then it may work.Sounds cool to own a place in Italy, but if something breaks down, there is a legal dispute - and many more problems.... you'll have to converse in a different language and different circumstances.