HOA will eat up a lot of your money. 

It will be very important to have both in place because of the fact I will be investing out-of-state.

Anything you do remote will come at a cost of operational inefficiencies and a higher cost of doing business.

I had found some regulations about VA guidelines and it speaks about recent separations and states that anyone who has recently seperated and doesn't have the needed 2 years job security can still be processed but underwrites will use their best judgement and will have flexibility.

Your rate will be higher than current, but give you your cash out to use for future opportunities. 

Everytime you sell you will be taking part of the gain tax free. 

How long are you going to own it and when will you try to sell it?

@Ben SyzekFor long term rentals in Colorado Springs you will need to find a deal at 50% ARV (This is very hard) or do a large down payment of 25-35%.

Finding a condo that allows Airbnb/STR will be challenging, they're rare and cost more because of it. 

Private (hard) money might help with renovation but will be pricey.