If you think prices will actually fall then maybe there is an argument for waiting, but I haven't seen any indication that that will happen.What is likely to happen is that the rate of appreciation will slow, but I do not anticipate it to turn negative (deflation).What is certain to happen is that interest rates will go up over the next 12 months.In the next twelve months it will not get cheaper (in terms of actual purchase price) or more affordable (in terms of monthly payment) to purchase real estate then it is right now. 

Your landlord policy will be more affordable as you're not insuring the possessions inside, just the structure.

After that I would determine your budgets - How much can you afford to pay in cash?

I recently used the equity from this crazy market to refinance out of the VA loan and into an owner-occupied conventional loan with the aim of reusing the VA loan to purchase another multifamily property.Here's where the dilemma begins.It seems like every month that goes by makes it harder and harder to afford some of these properties, so I would like to jump in and hedge against appreciation and inflation, but I am unsure how. 

I recently used the equity from this crazy market to refinance out of the VA loan and into an owner-occupied conventional loan with the aim of reusing the VA loan to purchase another multifamily property.Here's where the dilemma begins.It seems like every month that goes by makes it harder and harder to afford some of these properties, so I would like to jump in and hedge against appreciation and inflation, but I am unsure how.

I recently used the equity from this crazy market to refinance out of the VA loan and into an owner-occupied conventional loan with the aim of reusing the VA loan to purchase another multifamily property.Here's where the dilemma begins.It seems like every month that goes by makes it harder and harder to afford some of these properties, so I would like to jump in and hedge against appreciation and inflation, but I am unsure how.

@Austin SteedIf you can afford all the LLC's, the extra holding company is nice in case you get sued or audited. 

Some of the challenges:1) Pairing clients with properties that with an affordable plan yield the results the clients need2) Get the property into contract in this aggressive sellers' market with strong STR property buyer competition3) Deep due diligence to minimize property risk during inspection period + create best COE plan to yield the highest possible cash flow + start scheduling post-COE reno work4) After COE, get the hot potato moving- help in any way necessary to make sure my clients get this work done quickly and without complications so they can get their property on the rental market ASAP and start generating cash flow.5) Occasional STR audits as requested (always an option) by clients, to further boost their cash flow, and effectively their home value- based on income approach.

@Joe S.If you are looking for someone to purchase furniture, supplies, keyless lock, and set that up for you...then you might be able to ask your cleaner, handyman, or combination of both.If you are looking to determine if a home in a given market will make a good STR....I like to do that research myself.   

No one moves to Montana to buy a condo (who can afford a ranch anyway!?)