If you walked up to Michael Jordan and said, "I want to learn sports" he would walk away.

@Emily Paul here the best places for short term would be on the East End by the universities and hospitals, North Shore by the sports stadiums/AGH, or right across the river from Downtown/Oakland like South Side and Mt.

We definitely need to continue saving but I think you're right, wholesaling is my best bet to get started.

The best bet, especially with your first few buildings is the talk with your agent for an estimate

If you walked up to Michael Jordan and said, "I want to learn sports" he would walk away.

Heck I am willing to bet that for most of you your deal conversion rate is less than 0.5%.Your data,m is YELLING and SCREAMING at you giving you "in-your-face "hints"... but do you listen?

I would agree that in snowy climates a metal roof will be your best bet! 

If you were to conduct a market analysis of similar properties purcahsed with the intent to flip, I bet most were acquired with construction financing.  

They are not likely the ones to turn to in this situation because they don't see the importance of tax planning in your situation.I don't have a specific company in mind that works with 1031 funds but I bet a search on BP would steer you.

Regarding appreciation, it is always icing on the cake but you should never bet on it.