Simply, prices outweigh the rental income you will receive.

Not sure if there are tax benefits that outweigh the costs of keeping things separate between the the rental property and the side that I am living in. 

@Jack Martin We’d gain about 50K in NOI which would far outweigh the costs.

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!