Never send directly to them moneyfollow those steps and you will be ok if they are not legit.

He has suggested that to defer taxes I first transfer $150k from my current Roth IRA account into a new Self-Directed Roth IRA custodial account that I will open. 

Very new to this and talking to neighbors most folks (landlords and renters) use direct booking to fill up the 13-wk summer calendar. 

While some lenders can get creative with income and/or don't require personal income underwriting, DSCR lending programs technically only apply to SFR 1-4 units and small multifamily (usually to 10 units). 

The more unique the property, in both directions, the less accurate the zestimate.  

I suggest working with a Direct Lender that covers multiple states and offers the following support: DSCR Programs | PreApproval Certificate Letter to let you shop with an approval letter in hand and Prequalification support for Properties in advance. 

I initially considered looking at properties in Pueblo, directly south of Colorado Springs, since there are MFH's there that are significantly more affordable than in CS.

If it's on the MLS, investors have direct access to it via the listing agent or their own agent, so why would be able to buy it cheap and the resell it into the same market that it's already sitting for sale on?

So I just closed on my first rental property and have it posted on Zillow, it is in a desirable area and I priced it competitively when directly comparing it to other listings.

As it stands now, I am going to renovate the apartments, the tenants will pay me and I will communicate with them directly about all issues with the property etc.