Big difference It’s like seeing an ad pop up on google that says Google sponsored ad - it doesn’t mean Google recommends them it means they are paying GoogleThe same holds true for self directed ira custodians and others who may have on their website some names “sponsors” - a sponsor isan organization that pays a fee in return for advertising.

My husband has 100k in a sep IRA that we could convert. 

So to that end even though I think of myself as private I am in the business so I am a HML  the other folks posting on this site are all HML.. to me a PML is just that someone who is private and NOT in the business they they do a few deals out of their IRA for solo k a year and generally to people they know..

Do you think it is best to first max out Roth IRA before investing in real estate?

If they are not, you can roll over your 401k into a Self Directed IRA (SD IRA) and invest in real estate that way. 

I also have 401k/ IRA which put me on coast FI.So here is the question for you:Would you pull out 500,000 From the equity on the portfolio to do the following:Invest in Short term rental properties, in long term residential rental properties that are more aligned to appreciation.It would decrease cash flow by $2000 in the short term.

My only idea so far is to cash out the contributions we've made to our Roth IRAs, and pull the amount of qualified medical expenses from our HSAs (total ~$80k).

I bought my stuff cheap for cash, most over a decade ago.We still find distressed properties and motivated sellers willing to get rid of unwanted properties cheap that we fix up and rent out.I also use cash from my self directed IRA to also buy properties for cheap.

Will I lose depreciation deductions if I use Roth IRA fund?

Some of her properties are in her self directed IRA.