The depreciation could quickly outweigh the benefits.

Again, we come off as doing them a favor, when in reality, we are still above market and the cost savings of not having to hire a landscaping service far outweighs the "savings" they are getting on rent.

I think to tackle what you're after ultimately getting started and successfully getting your first investment should outweigh most everything else but that's up to your why in pursuing this in the first place.

Do the costs outweigh the benefits for your intended path? 

With that said, I agree with some here that the damage a pet can do can outweigh any fees you receive to allow pets but, you just have to mitigate your risks.

VA loan you will get a much better interest rate and NO PMI which will likely outweigh the small down payment a conventional loan will give you. 

In my opinion, the pros outweighs the cons as long as you weigh the risks appropriately.If you want the multiunit, go for it!

I do plan to switch to a pitched roof when the time comes where patching and painting out weighs the new roof configuration.

You definitely want to take a look at your debt and figure out if the return you would make on paying this off outweighs the return you would make on investing. 

The cons certainly outweigh the pros.