Use the search feature in the upper right hand corner and read some blogs and forum posts on the topic to ramp up your education.

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.

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.

Apparently, there is a market for hip "retro" features among people without taste. ;-)

Here is a start:  https://www.biggerpockets.com/rei/glossary/The search feature here on BP is very useful, that's how I found this link.