Yes, once you find a buyer, they can replace your EMD, but you need to have the initial EMD yourself. 

Quote from @James Wise: Quote from @James Hamling: Quote from @James Wise: California is on fire and they don't have enough water to stop it.

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

Is this a wise decision to use a HELOC on property number one that only has 20 to 25% equity in it to fund a down payment for a live in house hack in multifamily property number two?

Your solution is to borrow the downpayment, as well.This is referred to as "over-leveraging" and it's not wise.

Insurance is still an annual dog fight via my broker.Read your policy very carefully, consider replacement costs will probably be higher than estimatesResiliency is a requirement here.As far as sell or not....it'll depend on your determination to be here.This ain't the burbs of the bay area.Prepping for heavy rain right now.

I haven't done my first deal yet, but I hope that in 2024 I will be able to replace my W2. 

All water, sewer, and electrical infrastructure is being replaced.

Use this period wisely by ensuring your calendar is open, pricing is competitive, and your listing is optimized.Encourage Reviews: After hosting your first guests, politely ask them to leave honest feedback.

Future land appreciation in this area might outweigh any tax benefits from buying in other areas, with a better (tax-wise) ratio.Before pursuing your plan, talk to a real estate accountant to figure out if you can, in fact, benefit from cost segregation.