Personally I wouldn't upgrade from 08 to current if I had to pay unless there's some new feature you really need.

We have vacation rentals with lock-off feature in a few of our complexes here.Let me know if you would like a couple of examples.Aloha,Jeff

QuickBooks Pro has a feature called "Class".

If you haven't listened to the Bigger Pockets podcast from a few episodes ago featuring Sarah Prichett by the way, definitely give it a listen.

The property is 1,020 sq ft home  4 bedroom, 2 bathroom, condo that was built in 1953,  with an appraisal of $91,000 (Repaired), $70,000 (As is) .The only special features the property has  is that it has a basement and private parking which is a plus because most properties in  the neighborhood do not have.

There are numerous areas around downtown zoned RM which allows for more than one unrelated person.

There's numerous ways to find deals that you can research here on BP.I would network with some agents to get access to MLS properties that fit your criteria.  

If you have a lot of liquidity to offer, you can certainly pay cash but to your point that will inhabit the great feature of leverage.  

Also, I would suggest reading articles, latest news stories that feature these neighborhoods.

I know my husband would like to join you guys so keep us in the loop as we have done numerous flips in Illinois and Indiana also but we always love to network and share our learnings.