I'm thinking that you're maybe dealing with similar to Indy weather, so I'll tell you one bush here that works well year round and what most of our utility companies (at least back in the 90's and 00's) had running around electrical boxes in front yards. 

@Weng L.If you own both properties, then you can go ahead and dissolve the HOA as you have 100% voting power.

I told her I’d be power washing and painting the back deck this spring.

Yes, put less money down to increase your leverage (I hope you've read about the 'power of leverage' for real estate and how this sort of debt is 'good'). 

Selling in California and buying outside however gives me more buying power.  

He can turn a distressed company around with this power.

I’m just starting my real estate journey and I have this burning question that I can’t figure out.How do you know or decide whether you or the tenant will pay the utilities (water/sewage, electricity, gas, garbage)?

Example: can I charge a flat rate of $50 a month for electric if I only pay $40 a month?

Mine run on electricity and with maybe 14 loads a month and 2 lights it costs me $25 a month for the most expensive electricity in New England.

Our cash reserves can cover the extra expenses of putting in power and water lines(I own an excavator) and crushed concrete for the driveway amendment.