Just curious if the primary is more important as i move forward trying to use leverage in my benefit.

But the fact is that even if you have never taken the depreciation allowance tax benefit the IRS will make you pay it back when you sell. 

Once you are holding rentals, you get tax benefits (depreciation) and can defer some or all of the gain with a 1031 exchange.

You'll receive rental income and tax benefits, gain experience, and possibly see lower entry costs and lower risk.

The only big benefit of delayed financing is that on homes with a lot of offers, having a cash offer puts you to the front of the line.

Selling a property only to pay down another has no benefit financially.

My CPA told me that since my income is greater than $150,000 I would not benefit or be able to deduct the rental repairs and expenses on my taxes unless I form a LLC.

I bet if you said you had something to offer them to their personal benefit they’d reply back promptly

A contractor that you know and trust with no history of such things is another story, where I would probably just let the contractor know I'd made a note of it and was giving them the benefit of the doubt based on their clean history - further explaining to them that I had to take that action/stance as a gesture to the tenant, and that I value their service.

I am currently in the military and deployed looking to use my VA loan benefits to purchase a multi family home once I get back.