However, you will be able to count as income in the future. 

I just want my payments to count more, and not feel like im spinning my wheels paying off huge amounts of interest only

Apply the same requirements and count the support they receive as income for them.

Count on 6 months for a sale, divide profits two ways (make sure to include all costs and 20-30% more than your contractor quoted) and if it’s only a few thousand a month it probably wouldn’t be worth anyone’s time, right?

Hey Vikrant, Your STR wouldnt count for the STR loophole since its your primary residence, but the good news is the book keeping and tax situation would not be super complicated.

Here are some tips on doing comps when you do them:1. use the same bed count, go up or down a half bath2. start at a 1/2 mile radius from your target house (expand 1/2 mile each time to get more comps)3. start at 3 months back (expand 3 months more each time to get more comps)

We had already been planning to do some maintenance and repairs (repave driveway, re-insulate attic, replace two broken faucets, other minor items), but were wondering if, for tax reasons, we are better off waiting until we close on the new home and this is no longer our primary.Can this work count toward tax deductions as preparatory work on rental property, even if it's currently our primary?

if this was a rental property the gain on the property is whatever you sold it for minus your purchase price (broadly speaking)… there’re are various expenses you count against both your basis (purchase price)  and against your gain from the sale.  

My unit count is much less but the duration is around 50 years (combined my mom’s rentals and my rentals) without paying a tenant to leave or having to do an eviction.  

Then you take title to the new property counting both the purchase price and the improvements.I'll shoot a colleague request to you if you have follow up questions for off line.