Instead, be patient, do your own research (not simply relying on an agent) and only make offers that you are 100% confident that the property you are offering on is worth the offer you are making. 

But I've been successful with everything else I've taken on in life so I'm very confident REI will be the same.

I'm interested in meeting others in the area and I'm particularly interested in increasing my deal flow (hola wholesalers).

Prices have been increasing consistently in (or around) the double digits year over year, which should tell you something about demand.

Hence potential pool of tenants might increase causing more demand for rental property and hence rents would increase correct?

Some of his requests include asking to spray his exterior wood pile for spiders, replace a dryer knob, replace working doorbell, and increase flow of refrigerator water line.

You can do this 3 ways - decrease spending, increase income, or both.  4) Set goals and stick to them.

Some investors have money and are looking to make strategic purchases, knowing values and rents will increase over time. 

My cashflow will have increased though by maybe $4 - $5k/mth and would have to wait a few months before I have another 20k saved up for another down payment. 

If you are very confident in your estimates, then you may try to recalculate with a lower purchase price.