Now my dilemma is this, i can go regular conventional residential loan and pull cash out and get the standard 30 year 4.75 rate and be on the safe side. the downside is i have to wait 6 months for seasoning and also after 4 mortgages, which i plan on aquiring 2 properties per year, it will be hard to find financing( i was planning on having my wife put mortgages under her name once i reach this issue but realize they also use a dti ratio for their lending criteria so it is somewhat a gamble too ).Or i can go with a portfolio lender and get a commercial loan. i wont have to wait for that seasoning period, i build a relationship with a great bank and they are creative with financing so it wont be AS hard to acquire more than 4 properties.

I think you'll find that buying land for appreciation can be a huge gamble and a long term play.  

I'm not trying to be harsh, but subdivisions aren't something you do if you are inexperienced, and no lender is going to consider gambling away their money with someone that doesn't know what they're doing.

You are gambling on an upward trend in SD!

It can be a gamble as well.

You sure this is where you want to gamble your money at with questions like this?

Make sure that you close with a local title company who will offer you title insurance not just a title search, almost every time I've purchased something from auction.com there have been title issues that the bank didn't want to pay to clear but I've insisted, and they've relented.You either have to get inside the property before bidding, or you need to bid assuming you'll need to do a full gut rehab, or you need to gamble a bit.  

If you need appreciation to make the numbers work, you're gambling.

If you don't have access to enough cash flow and asserts to back the gamble.

Some value investors will pay cash with a primary term lease coming in a few years and gamble that the option will be renewed.CVS can have rent holidays you need to watch out for at the end of the lease.