What was done:Painted inside and outPainted roofReplaced flooring with new laminate, tile in baths and carpet in rooms.Replaced the tub, vanity and lighting in the master bath and tiled the shower and floors.Replaced the vanity and lighting in the guest bath and tiled the floorsPainted and repaired cabinets and installed granite counters and subway tile backsplash.Moved master closet door from the inside of the room to the bathroomRemoved original closet door in hallway and moved it to the master bedroom so that the master had a "his and hers" closet.One of the smaller rooms had a cubby hole next to the closet so you could fit a small desk and chair.

I got stung my dog got stung.. and its just a little hole in the ground in the shrubs so hard to detect until we saw them ingressing and egressing.. a professional had to take care of it.. don't know what it cost  .. 

Now of course you will need some monetary backing but you can also look for private money to partner with.  

Make it a monetary goal, number of houses goal, cashflow, wealth..etc... whatever you want the end of the rainbow to look like in your eyes.

Plus any cap ex would put you in the hole.#3 seems like a lot of work for not as much reward as #1

There may also be non-monetary factors to consider, such as the family members expected rate of appreciation for the property and tax considerations. 

I have been the handyman for almost 20 yrs for a property manager in Maryland, got lots of tales of what I've seen, even 249 nail holes in one townhouse and fixed them all at the tenants expense.  

Since I do not accept less than 5 night stay unless filling a small whole in the calendar I find 75% of my bookings are VRBO, 15%direct sales and 10% Airbnb. 90% of my 2-3 night holes are filled by Airbnb.

My mom, who not only cosigned to help me get approved for this home, she has also helped me out in part with my rent, and has been diagnosed by her doctor, after dealing with some stomach issues, that not only does she have some type of colitis or maybe something more, further testing is needed, but, she also has 2 holes in her heart, that will require surgery, and in turn will need to take medical leave from work beginning July 31st, which is the day of Her surgery.

It has many holes as Brian eloquently outlined above.