However, I’m wondering if anyone here has had success investing OOS in locations hundreds or even thousands of miles away and still managed to maintain solid cash flow.Have you been able to overcome the challenges of investing in a distant market, and what strategies or systems have worked for you?

If you are investing in a distant market there should be even greater reasoning behind the investment because you have less control and therefore even greater risk no matter what anybody tries telling you. 

So you want a QI with demonstated experience and enough staff to be both responsive to you and to work with those distant closings.  

Unfortunately, 99% of BiggerPockets posters who are not local to Philadelphia and choose to invest in Philadelphia invest in the lowest tier neighborhoods, just as they do in most other distant markets where they invest because they are lured in by the inexpensive cost of housing. 

Quote from @Michael Eldridge: Switching tax preparer this year and since informing the previous one over a month ago they have been distant.

Instead of juggling that distant duplex or diving into flips, what if you sold it now (or soon) and rolled some of that equity into a deal with us?

Moving the house only a short distance on the same lot should be MUCH cheaper than moving it somewhere more distant. 

Business comes first, taxes a distant second or third.

So, the question is not whether to invest remotely, but where to invest.Investment TeamRegarding properties in distant cities: While books, podcasts, seminars, and websites offer general knowledge, you'll ultimately purchase a specific property in a specific location—each with its own unique conditions.

Practically speaking I think that's more than enough liquidity.Another angle is Roth dollars are so valuable you never want to withdraw them until the distant future, but you also don't want to contribute more via MBDR and instead have more after tax?