Just wanted to get a grasp of what criteria Hard Money Lenders look at when qualifying someone for a loan.

Good luck finding your first commercial loan that does not report on your social security number (ie: your name). 

I bought it in 2021 with a conventional loan 20% down.

So we (wife and I) are ready to make that final push towards retirement with long term buy and hold properties!!

We can get a second home without putting anything down (VA loan), move into the school district we want and a much nicer home for our growing family:Current home (want to rent this out):One of the largest lots in the area 1/100 lots in an area with 1000's of properties that has navigable water which is our water, at 2.75%, 280k remaining $1650/month, rents $3000 mom will be lending 25k over 5 years at $500/mo payments, and we will use a property manager $300/mo = rental take home of $550/mo incomenew home (hypothetical estimates):$550k @ 7%, paying ~$3300/moWe will have a period of 9 months starting Dec 2024 where we would be at about -$100 where our older daughter goes to pre-k for $1150/mo and infant is in daycare for $1650/mo.

I sold this property on a lease option/contract for deed conversion and refinanced the house out of my hard money loan.

I would also seek a lender who can explain the range of loan programs available to you.

If I can turn my current home into a LLC what are the pros and cons, and can i use a conventional loan again since I'm no longer the primary.

You can easily qualify for a dscr (no tax return, no dti, no proof of income) loan, cash-out, use that equity for down-payment on other STR's.  

30-year VA Home Loan Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?