This is a business and no point in running in the red. 

County (delays and red tape - though you can of course not have to deal with this for most improvements)-Prices are very high-Tenant-friendly state - it takes much longer to evictPros:-Tenants tend to stay longer-Property taxes are low VS purchase price-You can quickly fill a rental as demand is there - no matter what the asset class is-Utility companies are super helpful.

You can discuss the policy but do not bring Dem/Rep/Trump/Biden/Conserv/Lib/Red/Blue into this conversation.

Absolutely no way...if you want to be in the vacation rental business, jump in - but why would you allow the wear and tear on your property, the potential code/zoning enforcement issues that can arise, the risk of being cancelled by your insurance provider and more. 

Also, applied for a LOMO to get it out of flood zone.

A multi zone mini split system would be easy to retrofit into a brick house, it is also a super efficient way to cool and heat.Older brick homes are also good candidates for a “space pack” system, with ultra slim flexible duct work.

I spoke with the city and since the property is on .8 acre it can be zone for a 3 family.

Red flag #1.She constantly asked me how to do things. 

The current use is legal and in compliance with the zoning ordinance in its current condition and occupancy.I am acquiring an FHA loan which is whats making getting the loan approved a tricky one because of the zoning issue.

Happy to provide more info about myself, but will cut right to the chase:In today’s market, if you see a property listed for 4 months with 2 separate pending sales that did not go through, is it safe to say that is a red flag?