I'm feeling red flags here.

So the sign - while it may make someone feel warm and fuzzy inside - doesn't actually do anything to solve a problem. 

I am very excited to begin this journey because I’m ready to start living financially free and start a job that does not feel like a job!

I feel like this is the perfect time for a win/win creative finance deal.

It also can get challenging to set a price now to possibly buy in the future that the owner and you will feel is fair (with markets still appreciating at a healthy pace).You can also keep your eyes open for a seller willing and able to do a land contract with you (but there usually would want much more money down and likely want a full pay off in a few years, but can see what you can negotiate on terms).I agree nothing illegal about options/option fees in WI to my knowledge, but generally seem much less frequently used in single residential transactions than commercial transactions where due diligence and closing timelines may be very drawn out.

I feel like giving the listing agent's a hair more may be the best of both worlds, but that's the most plain sighted answer. 

While it is OK for the legalities, I feel that the safer the pool area, the better.

Just feeling extremely weird.but buying a condo or house is almost double or triple the money.

In general home warranties suck...... the people they hire to "fix" the issue suck..... the job they do suck....customer service sucks.They band aid the issue at best and then charge you every time them come back and fix the issue again.If you run the numbers, you are often better off setting the $$ aside and paying straight up for any work needed.Every so often you will have someone that has it "pay out".... they replaced the 4k HVAC system etc..... its rare....like winning the lottery.The House always wins...... they make gobs of $$ because what they pay out is tiny compared to what they take in....that's how insurance works or no company would be doing it

This just feels right but obviously has to make sense.