My concern is buying a property around the lake communities (IL, WI, MI) and not having it filled during the winter months. 

If you lie and move into the home, the lender will use this as a defense.I’d be more concerned that you are buying a long-term investment property with hard money when it doesn’t appear you have a viable exit strategy.

Some are going from $1, 000 or less in rent to $1,650 which is concerning to me.

It is good that I know I have someone that is interested in buying it if I ever need to get out, but I have some concerns because he is the one that runs the HOA.I had a few questions for anyone that has experience with condos and HOAs.Should I be worried about the HOA increasing and eating up cash flow?

I looked into a more stable cash flow market such as Indianapolis but the crime index concerns me.

We're concerned about the difficulties involved with selling and buying in the given time frame, etc. and are hearing about delayed and reverse 1031 exchanges.Does anyone know of a good resource or contact that we should be checking out to learn about this process?

Therefore water/energy efficiency is of the tenant's concern and not mine, in addition to the condition of fixtures within the suite. 

I understand that I cannot take more money out than my Purchase Price for the property with Delayed Financing and I am okay with that.My concern is that under the DF rule, if cash used for the purchase of Property A came from a HELOC or Refi, then any money that I receive from the Delayed Financing needs to go towards paying down my Cash Out Refinance on Property A. 

I think looking at properties that have been on the market for awhile especially can yield opportunities since people will assume something is majorly wrong with the property and ignore it - I know I had those concerns like what am I missing here?

I'm concerned that because both tenants are long term they would be difficult to remove and I'd have to go through the eviction process.