And how and where does the HUD program come into play that can help me?

It could be easily played at thousands of wedding receptions during the father/daughter dance.

As it played out I had an investor step in and purchase 2 units that still needed rehab,  cash deal although at wholesale price.  

Well, are they really want to sell the property or just playing up??

Its not a place to start out but a good goal for you to have to maybe play in that market.

@Sezuo Daudu like most investors on (and off) this website, and especially in Chicago...anything outside of “A” And “B to B Minus” areas just literally don’t exist to them.With $150k in funds you can almost two buildings if you play your cards right.

We've been using Cozy for about four years and it's been a game changer for us.

It would be a vanity play, stoking our egos to move into a nicer house. 

I think the sweet spot is 4-5 bedrooms, 3-4 bathrooms, a fabulous Master Sweet (since they are likely footing the bill), sleeps 12 - 20, tons of activities (installed a pool table, corn hole game, etc...), and in my location of AZ a pool. 

If your portfolio is a good deal you won't have an issue finding buyers.If you truly have control of a package is one thing, if you are trying to play match maker with no real control, that is a weaker position.