For my first real estate investment I've decided to wholesale my first property, and after searching for properties in my desired area, I located a few but they're all on Auction.com, which brings me to my questions.

You already have one great team member in place, and if you have a true desire you are on your way.

I agree with you that a multi step mailing campaign will always out pull a once and done, however, if this is your first campaign and you have a mentor that is doing what you aspire to, I might defer to her.You can do exactly what she says to get her results (if they are desirable to you) and then improve on what she is doing from there.Early on I had a mentor who I listened to exactly and I owe a large portion of my early success to listening to his advice verbatim.

Based upon your courage to have two rentals by 20 and your desire/ability to leverage your artistic and hands on talent to improve projects you will certainly go far here and be a valuable asset to the local community.

In SW Florida, I expect prices to continue to rise for some time further squeezing out certain people from being able to rent in the more desirable areas.

Everything desirable is too high for me, since I would like to pay cash (max 250k)  (bad credit risk due to no income) Kensington seems to have some good deals.

@Andrew ChallengerOkay, now I see why sub-leasing might be desirable to have: to let someone else burn-off the remaining 3 months.I hadn't considered that the students might want to have their own room without a roommate.

Of course for multifamily finding a 9 cap on a stabilized in a desirable area is really tough.

I let the newbies and the poorer people tangle with the less desirable properties.

The investor must decide the desired cap rate and CoC return and whatever other metric he wants to use to decide the price at which he wants to acquire the property.