Investment Info:Single-family residence buy & hold investment.

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

I'm very new to investing and weighing which options would benefit me the most.Option 1:  Use the cash as down payment on another primary residence and rent out the current.

Since you are renting out part of your primary residence in Maryland, your main concerns should be liability protection and tax compliance rather than complex asset structures.

The only way I can access is money is through my primary residence and doing a HELOC.

Investment Info:Single-family residence fix & flip investment.

Investment Info:Single-family residence wholesale investment.

While you did point out the negative aspects of a deal like this, you didn't really highlight the pros on the RE side and future investment, appreciation etc.I’ve done two of these projects in the past 3 years in SoCal.

I'm a former NorCal resident now up in Tahoe on the Nevada side.

You might decide that you absolutely want to own your own residence there and I assume you can afford it since you already own properties elsewhere, likely in beautiful Hawaï.