Both have section 8 renters which I prefer since that program pays me directly and I don’t have to worry about the tenants paying the rent.

I would recommend learning a bit from here and making your PRIMARY authority on this your real estate or business attorney (preferably with a Tax background). 

Preferably one that advertises as a specialist in that area and that has good reviews from Landlords and bad reviews from tenants.

I'd typically prefer a SFR that was a great deal, but I'd buy a condo if it made sense too.

The other thing that you could consider is replacing all the blinds with new ones of the same (matching) type, and if so I'd suggest something like a cellular shade or a roller blind like mecho-shade (that's a personal preference). 

Most REO deals prefer cash or private or hard money.So, many new investors think foreclosures are good because they are priced lower, but they are disastrous options for first-time investors as the inspection ability and repairs requests are limited to none and foreclosures also often times come with tax liens and other liens that may all not be fully disclosed at the time of the auction.If you are a first-time buyer and want distressed, you can look at HomePath properties which are Fannie Mae REO and they can provide a bit more protection to you as a buyer.

I would prefer analyzing in the north east of the US since that's where I plan (currently live in NY) on doing my house hack but whatever gets me started I'm willing to help as well.

I would prefer to hold on to some of that cash however for the repairs noted above. 

Many banks will strongly prefer a shorter amortization (usually 20-25 years), but there are banks in most markets that are fine with a 30-year.

Do the Seller's want all cash now, or would they prefer to do some owner finance over 5 years to make a little interest and reduce their tax bill?