Decided just jump straight into RE (part time for now) after that.

Buying a property.that probably wouldn’t qualify for a traditional mortgage with cash, private, or hard money and refinancing it after the rehab with a cash-out mortgage is pretty straight forward.

Don't go straight for the neck because remember, these homeowners are tired, frustrated and scared.

You flip the first prop (Prop A) for a $50k gain - you pay taxes on that gain because it's a straight sale, no 1031 there since it's a flip. 

Reach out to the HR department of the team...that's the only way you will get a confirmed answer.If you want to rent to athletes in the position, you will need to plan for a high rate of turnover.... its the nature of that job....guys are gonna get cut, traded, injured etc etc.... they move a lot.....You could do a higher deposit to help cover penalties for early termination...... do M2M with a higher rent than you do for a year long lease.Or be honest and straight up tell them you are only looking for long term tenants and due to the nature of their job, the probability of that is not high, so decline to rent to them.

Your agent should hopefully understand that you need to get your bearings straight and understand the market in terms of what houses at certain price points look like.I also agree with what @JD Gunter mentioned, in that it is all relative! 

@Dave Lawrence, The proposal sounds pretty straight forward, it should work just fine.

It came straight from public records like all the other comps.

@Heather Schmidtknecht Be straight with the listing agent and introduce yourself as an investor.

From there the amount is diminished until you reach 150k in income at which point you lose the ability to write off real estate investment losses against your income taxes.I went over this example numerous times before posting the question as I wanted to try and get my facts straight.