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

Because of this, I'm exploring what it would look like to begin investing in vacation rental real estate as a way to:1 - Save on taxes by taking depreciation2 - Hold long-term appreciating assets3 - Have properties where we enjoy vacationing that we can stay at when we go to do maintenance (probably 2 areas).What resources would you recommend for someone just starting out who has these specific goals?

I appreciate your thoughtsSorry for another question, I still beginning my searches about this subject, in this case do you have a LLC holding managing all other companies or all of your companies are totally independent?

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

You can not hold them until your death and leave them to your heirs tax free, they must withdraw them and pay massive taxes or sell them. 

Investment Info:Small multi-family (2-4 units) buy & hold investment.

This is what I think I know:- The borrower can choose to pay off the note at any time (by selling the property or just paying off the loan with other funds), so it is important that the legal balance covers my investment and some profit- The borrower could file bankruptcy (can someone confirm that this will only cause delay, but not jeopardize ultimately collecting the legal balance of the note)- Most of these DOTs will have a rent assignment clause, so I could try to enforce that and collect rents from tenants (essentially manage the property) while I am holding the note and trying to foreclose.

Getting a hold of someone that is knowledgeable on your specific questions and can give concrete answers will never happen in the NYC DOB.

Benefits: This strategy is particularly useful for high-income years, as it allows you to defer taxes and increase cash flow by reducing your immediate tax burden.A cost segregation study can be especially beneficial if you plan to hold the property for several years and want to maximize deductions early, but just doing cost seg is not helpful.

If you’re planning to hold the property long-term and want to avoid potential roofing issues down the road, I would lean toward the standing seam steel roof.