One idea would be to start to strategically pick a few of your SFH's and position them to convert into your primary residence periodically.  

Hello everyone I have been reading bigger pockets for awhile and I am interested in eventually buying real estate to buy and hold long term.

any prior blog or metrics on how the trends appear for Multifamily units to be converted for STR purposes would be helpful. 

The plan is to get a HELOC and buy a new personal residence and convert our SFR into a rental.

Perhaps you could have underlined the words “until the property is sold” and added a fine print that when the property is eventually sold the taxes due will be more than the taxes saved because depreciation recapture is taxed at a higher rate than long term capital gains rate 😏Here is a an example of someone paying thousands of dollars in tax preparation each year in order to record the paper losses noted in K-1.https://www.biggerpockets.com/...

And that is, finding a property with a detached garage or a basement with a separate entrance/exit and converting that space into an additional dwelling unit (called an ADU) which I can either rent out short term on airbnb/vrbo or longer term.

We are confident that we will eventually find good tenants and there has been a lot of interest but only a handful have completed the application process.

My dilemma is whether I should just go for it right off the bat, which will save me some money, or make it a master suite first, and then convert it after the appraisal.Thanks for your time.

My mortgage broker told me to simply get the "second home" insurance policy in order to secure the mortgage and then change the insurance plan later.So now I'm looking to move it into an LLC and convert the insurance policy to an STR, but I'm a bit worried about the implications.The lender said it's fine to convert it to an LLC and that this would not cause any changes to the terms.

Eventually, you have to just pull the trigger and learn as you go!