Beyond the tax incentives, Spring is an excellent time to close on seasonal areas (such as the Oregon Coast) where high season is typically from May-Oct/Nov with the peak in June/July & August.

Maybe you offered too much to the homeowner.

My wife and my professional careers offer *positive thoughts!

They will offer to stay with a friend or family member.

There are other options like Citi and Navy federal that offer secured cards that graduate but some take a long time to graduate.

A family friend of mine who is a long time real estate investor with several properties has offered to sell me one of his properties.

In this scenario does it make sense to buy a triplex or 4plex in a less desirable/up-and-coming neighborhood , rent all units out while I continue to rent in center city/fishtown/UCity/NoLibs? 

I think it's the best way to get started when you don't have a ton of money to spare, and you are still learning.1. look up on facebook marketplace what other people are offering their rooms for, that will help you get an idea of what you can charge. 

Or incentives go a long way to shore up a longer lease.

I feel like it's a way to keep people on the platform and appeasing hosts, instead of offering more supportive customer service.