It doesn’t matter if you buy a new roof in year 5 or year 30, you depreciate it over 27.5 more years, not 27.5 since you purchased the property.

Therefore, you don't need to use a 1031 exchange; you can take as long as you wish to find and then buy another property.The only exception is if there is debt on a property, in which case there will be some UBIT (Unrelated Business Income Tax) implications.

Buy a 4-plex with an FHA loan.

Start getting to know realtors in that area and give them a Buy Box you're looking for. 

Hi Shea,It is a residential property and, yes, my strategy is buy and hold.

If you are buying loans then its more complex as you have discounts involved, monthly cash flows, outflows (like servicing costs) and unknown exit dates.

Airbnb is a company so the only way to buy one would be to own stock in the company. 

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

I had a similar strategy with my first few house hacks: buy in great A & B Chicago neighborhoods....get by with minimum cash flow, and wait...What's your plan for the next purchase Michael?

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