Although you could probably find better investments on paper, vacancy & turnover expenses are some of the most costly parts of owning investment property, and very difficult to forecast with perfect accuracy.

I think I can get a policy online with the other requirements, but this waiver seems to be more difficult to find.

In the short term, I aim to replace my monthly income from my current entry-level job, I dont make a ton of money so this shouldn't be too difficult.

Out of state seems harder to break into simply because I'm not there - maybe Hoboken /Jersey city or further like @Eric Hajdu mentioned are better places to start.Out of state is not difficult to get into. 

and it's also difficult to find 80% LTV these days.  70-75 is more likely. 

SFR is much more difficult because of taxes, purchase price and rent generate but if you are open minded to a rent by room strategy or mid term rental strategy SFR can look more attractive.  

Quit transparent on everything.If you understand DST and UPREIT route, this is not difficult to understand. 

Do you know if there is a lot of red tape which makes it difficult or is it fairly easy if you meet requirements and lender knows what to do? 

If buyer won’t accommodate time frame, making it difficult, then we may get picky unless buyers agent convinces me otherwise.

I know that here in our area, snow removal services are difficult to find for residential areas.