Is it smarter to buy a house all cash now, with the plan to take a loan out when the market inevitably cools/crashes and interest rates are lowered? 

Are we talking about tax planning strategies?

My plan is to live in the house for about two years, possibly engaging in month-to-month house hacking during that time before transitioning to long-term renting.

Assuming I am understanding you plan.

Hi All,  I am planning to move into the seller financing strategy to generate cash flow and am looking for advise.In today's world of Dodd-Frank, what is a good finance term?

That is the plan, i.e. buyers are persuaded to purchase a home to take advantage of a credit to their taxes a year later (they still need the money up front remember).

 My concerns and focus in this phase of my life is long-term financial planning - retirement etc (46).I dont have any retirement savings except my job offers a State Pension and I own 2 single family houses.

Seems like the better plan would be to go to the city council meeting and prove to them that you are not running a STR.

It just happened that im in the process of purchasing 2 properties this month. 1 is a rehab, that I plan on keeping for my self for a bit then selling.. the other is an invest property non owner occupied thats a 3 familyThe rehab I need to purchase out cash 105k and another 15k-20k to repairThe rental property I need to put 25% down and closing is around 70kSo I need 175k to purchase and another 30k to repair both properties I have 90k in liquid in a savings account,  230k in a 401k made up of the funds and stock and about 330k in my companies stock account..My plan was and not sure if this is the smartest way .. hence why I'm asking here!

The road is not in, the water main not installed, the sewer main and laterals not installed, etc.Just having the engineering done, and the plan approved, adds significant value to the land, and makes it attractive to a developer who now, doesn't have to go through all that work.