Also, take into consideration how well maintained the condo association is as this should be an indication of the financial stability of the association.

The $1M spend by the tenant may indicate plans to stay or cash out on RE to balance books.

I wouldn't use that as an indicator. 

If you're hesitant to do that, it may be an indication that it's a bad idea. 

@Sarah Bower  The questions you're asking indicate that using a Realtor would be in your best interest.MLS is one of the most effective marketing tools there is for residential real estate, but there's a lot more to it than that.Knowing how to price the property. 

The written proposal must indicate Work Items that require permitsand state that repairs are non-structural.

Underwriters generally rely on an affidavit from the Seller that the property is his/her/their homestead though if the title search indicates the property may not be homestead they may make additional requirements. 

@Kristen Crotts Based on how I am reading your post, it seems like you will be moving out of your existing house hack to owner occupy your new rental and that is why your lender is indicating you'll be able to get in for only a 20% down payment rather than the normal 25% down payment required for an investment property. 

The report came over from the HOA and said yes, this would have been long term damage, not something that happened in a weeks timeframe.We are at the end of the lease, but they have not indicated any interest in moving out. 

Anything you have read indicating different contribution limits is either incorrect or something you are misinterpreting.It is typically about a 3-4 week process to setup a new plan and get it funded via rollover from a prior plan.