That comes first.If your tenant has done any damage, it's already happened and it's likely not as bad as you are imaging.Some areas have eviction services where you can hire someone to handle the entire eviction process for you, from the very first step of filing and serving notices, to the court date, to the eviction day itself.

Additionally, only my aunt's third appears to benefit from the 250k capital gains exemption.The house has appreciated approximately 300k in the last 16 years. 

You need a writ issued by the court.

Here is a breakdown of the items they saw that needs attention.Needs minor trash removal; needs mownSupport post trim needs replaced; badly deteriorated; upper trim needs scraped and paintedBroken panes on side back needs replacedReplace fixture on front porch; flood lights on backNeeds some minor trash removed and minor work done220 wiring needs secured;not up to code, needs to be placed inside conduit.Install new furnace filterClean and paint register ventsInstall apprx. 4 door stopsFull interior rent ready cleaning required after all work completeReplace as needed to match all light bulbsSteam clean all carpet; sweep and mop vinylReplace missing storm door, paint interior doorPaint all wallsPaint door; interior shows signs of previous leak, but doesn’t appear to be a current problem; paint interiorSeal gaps in side window; paint all; seals appear damaged on double pane windows; may not be an issueReplace screensInstall two smoke detectorsInstall two blindsTouch up, as neededPaint all window sealsSeals appear bad; paintInstall screenVery old and drawers fall out; should be replaced with new; secure handles, if keptHas several large chips; functional sink otherwiseInstall two strainers Install fire extinguisherPaint side exit doorEstimated cost is $4,000. 

Mathew, great advice, and thanks for letting me know what those units are called.I googled PTAC units, and it appears they run approx $700-1000 per unit (for the ones that do A/C and heat), plus additional materials, installation, etc. 

This requires immediate action, your lawyer may need to send important legal notices to the Seller and/or file an LP in court. 

SFH debate given the condos appear more like houses vs. boxes in a high rise.Anything specific to look out for with the ownership structure?  

@Tara Wright yeah, it appears the mortuary has ample parking along with the SFR I am looking at.

My lease states that written permission needs to be given, so there is no "he said, she said" in small claims court.3)  That's going to be another tough row to hoe unless you have a sales receipt. 

I hope im wrong but I see a good court battle coming up