In some cases, the original owner may have a right of redemption period that extends beyond the sale.

Some quick and obvious ones include: 1) not being able to find a good contractor2) even if I do, not being able to get him/her/them to walk the property during the diligence period to give me a thorough scope of work3) if I need to back out of the deal after seeing the inspection & SoW, that particular contractor not wanting to work with me again and then me having to start the contractor-finding process all over again4) not being in a good position to manage the contractor throughout the process, thereby leading to an over-time and over-budget (and potentially incomplete/subpar) rehab.I could go on but you get the picture.

Make sure you understand exactly what a tax lien is and how it work, redemption period, etc etc. 

I'm assuming the 2-year wait period will apply whether it's a property I'm buying off the MLS or an unmortgaged property I already own.

That said, if the seller is willing to accept your stated financing terms, then get them to sign a purchase and sale agreement NOW and just give yourself enough of a due-diligence period to figure the rest out!

Also, if you do a cash out refinance and do not find a deal for an extended period of time, that is a lot of cash sitting around and losing value.

I have VERY recently started acquiring property through judicial foreclosures, where I am bidding on the second position and acquiring the property subject to a first mortgage/DOT ( and a 6 month redemption period).

Another loophole is to buy a second home which only requires 10% down and use it as a STR and after a short period of time just convert to a long term rental.

There is, and always will be, some percentage of the population that will not conform, period.2.

This area used to be filled with mom and pop investors with 1-2 properties but now big money and all cash seems to be winning out on almost every deal I see in the greater GR area and from those that are ok holding for a very long period of time.