The earlier properties in one’s career can require walking a thinner, riskier line before a base of core assets are under an investors general belt.

You have a duty to perform for your investors and if the deal is thin, that might mean tightening your own belt buckle. 

Im still new to the game so I don't have experience under my belt. 

Get into investing, get some experience under your belt, keep growing your capital, then reassess.

Get a few months under your belt, get the lay of the land, see who the good tenants are and the ones you want to keep offer them a long term lease. 

Although it's a strategy that's good for beginners, there are plenty of very experienced RE investors who continue to HH.Plus, if you do decide to BRRR a property in the future, you'll be much more prepared to do it if you have a HH or two under your belt--a ton of the lessons you'll learn from a HH can be used to successfully execute a BRRR! 

Seems like many banks are tightening their belts and aren't offering programs like this. 

Get at least a few properties under your belt before you start worrying about how to save taxes like Trump.

I think at the time I was nervous about doing a total gut rehab but now that I have this deal under my belt I would go for a nastier place so I can add maximum value and then pull my money back out at refi.

One of the tools in my tool belt is a lender that will provide a proof of funds for the full amount, assign you the contract and then lend you back on the property with a 21 day close.