However, as you mentioned, this will involve two sets of closing costs—one for the rate and term refinance and another when you eventually cash out refinance.

When I'm working investors the first question I ask is: "What does your money need to do for you, how soon does it need to do it, and how involved do you want to be along the way? 

He has another brother that is part of the Trust and he is okay with what my dad decides; he isn't involved at all but my dad wants to be fair in the situation and it would be fair market value for the property and do everything above board.My wife is a realtor, so we have the benefit of her selling it.

Philly requires a period of 30-day "eviction diversion" program phase.

While I prefer to see properties hit the open market as that's often where the most value is realized, I have seen deals that made sense for all the parties involved that did not hit the open market.For returns, commercial investments do operate differently than residential, and the primary difference I see is the emotion vs. numbers of the deal.

Str’s are riskier and much more involved than ltr’s.

With a card, there's a third party involved in the payment, which means chances of something going wrong have just gone up 33%. 

We are currently in the diversion phase (30-day Philly requirement before filing in eviction court).

However, they might not appreciate as much over time, and the market can be a bit more unpredictable.Ultimately, your choice depends on how much risk you’re comfortable with, your long-term goals, and how involved you want to be.

My personal taxes involve fairly complicated investments that also require multi state filings.