I have no experience there, but that is by choice.

The smart kid who doesn't want to loose all of his hard earned marbles has to play somewhere else.

I don't have very good credit due to poor choices when I was younger.

Assuming the rents cover your expenses, in 30 years when you’re in your early 50s and the mortgage is paid off, and you’ve done the smart thing by raising the rents over the years, you will be sitting on a multi-million-dollar asset that cash flows thousands of dollars per month at the cost of a measly $20k or so out-of-pocket when you were 20-something.

Seems like every time I put an offer on a property that is less than asking price (or even when it is asking price), they come back with "send your best offer".I get it from their perspective, it's a smart response, but what's the best way to respond to this?

Thus, creative mailers are indeed a way to get the phone to ring and upon answering it is fairly contingent on your choice of area to farm and closing tactics to convert those RR to CR, and eventually snag that wholesale contract. 

I'm having faith that whatever I decide, it will work out as well but I must be smart about this, can't throw it all in the air and see what sticks in this situation.  

Do I want to buy the house for more that $450,000 (if I'm given the choice) so that when I sell it and there's a gain I won't get nailed in taxes? 

Removing PMI is a smart decision it's money that does nothing for you.

We can still fund a deal with this type of structure although the funding fee increases, That is why #1 and #2 are preferable choices.